Category Archives: Leadership

The Two Most Important Words for Product Managers to Use

8 August 2019

What does your sales team think of you? Does customer success enjoy their conversations with you? Or do you feel animosity and tension with them?

And what about with customers?

How about the squeaky wheel who sends in feature requests regularly, or the enterprise customer with contractual promises?

Product management is about relationships.

One of the biggest mistakes I see otherwise good product managers make is not managing internal and external stakeholders well.

Rather than building collaborative relationships, where everyone feels like they’re on the same team heading in the same direction, they sow seeds of tension.

As a product manager, any communication issues fall on you. It’s your job to build bridges, even on challenging terrain.

You can do that through a variety of tactics:

  • Product advisory boards, and regular check ins with key customers.
  • Peer 1 on 1s with key sales, customer success, account management, and other department leaders.
  • Regular updates, training, and collaboration on collateral creation for new and updated features.
  • Following the timeless of advice of Dale Carnegie’s How to Win Friends and Influence People.

Throughout those conversations, both internally and externally, there are two words to always remember: “Not yet.”

Let’s dive into the nuance of how 4 letters can make such a big difference…

“Not Yet”: The Two Most Important Words for Product Managers to Use

Remember when you were a little kid and you wanted something and you asked your mom or dad? How did you feel when they said “no”?

Chances are you were pretty unhappy.

We’re not so different when we grow up.

Just say no…to saying, “No.”

As a product manager, when you tell customers and colleagues, “no”, it creates problems for you now and in the future.

No is denying what they want.

No makes them feel unheard.

No is a wall between you and them.

And most importantly, no is the end of a conversation.

Where do you go after you say, “no, we’re not doing that”? You can possibly explain why, but the other person is likely already thinking about how they can either convince you to change your mind or tuning you out in frustration.

The Power of “Not Yet”

Four letters. That’s all that separates “No” and “Not yet”, but in reality it makes all the difference.

Not yet is, “we might do that down the line…”

Not yet is, “I hear you, but…”

Not yet is hope.

And most importantly, not yet is the start of a conversation.

“Not yet” builds empathy

If you’ve ever learned about the power of using “and” instead of “but” in conversation, you know that a simple change in word choice actually leads to a larger transformation.

By changing the word you use, you change the entire nature of your discussion the rest of the way.

When you say, “not yet,” it lends itself to explaining why. This is powerful because it helps them understand the choices you’ve made.

When it’s an internal stakeholder, explaining why can help them see the other priorities. I’ve lost count of the number of times that once I’ve explained what we’re doing right now already they suddenly are willing to wait on their request; you may even be working on something important to them.

Meanwhile, with customers, it’s an opportunity to build excitement and engagement. Maybe you can’t give them what they asked for right away, but you can tell them about some other things in the pipeline.

Often, a couple of the things you’re doing are also important to the customer. You can then offer them the opportunity to provide feedback on the feature as it’s developing, or early access. Either way, it ends up feeling like they’re coming away with something, even if it’s not what they originally asked.

Show your work.

A key part of all of this is that you’re showing your work to others. You don’t need to explain the whole roadmap, but even a small snippet can help people see there’s a solid foundation to the decisions you’ve made.  It also demonstrates the hard work and rigor of the product team:

  • Data driven: Good PMs know their numbers, so you can explain to them how the feature they asked for may have a much smaller impact than the current features you’re working on.
  • Customer focused: Whether you have an enterprise contract with deadlines due in 30 days, or are finally delivering on the #1 most requested feature, showing that what you’re doing is backed by real customer insights shows you’re a PM that listens to customers.
  • Strategic: Great PMs see the big picture, and help others see it, too. Concisely explaining strategy comes with practice, so use these “not yet” conversations to practice clearly explaining how the new API opens up thousands of leads a month, or how the onboarding improvements will drive more revenue to hit key company goals.

When you show some of your cards to your colleagues and customers, you help them understand your decision making process. While they may not always agree, they’ll often respect the decisions you’ve made a lot more than when all they heard was, “No.”

In my experience, when you show you have data, strategy, and customer insights backing up your decisions and bets, your colleagues and customers will trust you. Just like they expect you to trust them to do their jobs well, they’ll see plenty of evidence to believe in you as well.

Save your relationships!

This may seem like a small thing, but I can tell you from experience,  it matters a lot. No may feel like the expedient way to handle requests, but it comes with a long term cost.

Over time, saying “no” leads to resentment and may sour relationships. People you want to partner with to make launches successful and for everyone to hit their numbers suddenly avoid you, except when they want to demand and override your No’s. They may even try to go around you and talk straight to a designer or engineer to get what they want.

And since you represent the product team, it can even lead to inter-departmental drama and rivalries. Rather than engineering and sales being partners, they become enemies, with each side criticizing the other. I’ve seen and heard it too many times, and it’s really the fault of product managers on those teams for it becoming like that.

You can avoid being that kind of cautionary tale by taking the time to regularly communicate with other teams, stakeholders, and key customers. When you meet and talk with them, remember to use “not yet” so those relationships flourish and they understand your decisions.

Never underestimate the power of using the right words.

Peer 1-1s: The Missing Habit Separating Good and Great Product Managers

24 September 2015

5 Comments

There are many skills that go into being a great product manager, and one of the most underrated is communication, as these Silicon Valley product leaders emphasize:

“As a product manager, it is imperative that you understand the company’s overall goals and objectives and exactly how your team fits in to the broader vision.“ – Josh Elman

“We lead by example. We succeed by making others successful. We listen first and make certain that others feel that they’ve been heard. We pursue diverse opinions. We rally our teams behind a vision that yields passion and commitment. We value and foster strong team relationships.” – Satya Patel

“Good product managers communicate crisply to engineering in writing as well as verbally. Good product managers don’t give direction informally. Good product managers gather information informally.” – Ben Horowitz

You can be the best former engineer or designer, but if you can’t communicate, not only with your product team, but the broader company, you’ll struggle.

Great Product Managers communicate beyond their teams.

While it’s important to develop great written communication skills, informal, verbal communication skills are just as valuable.

When you are working with other departments to either gather customer insights or share with them a new feature launch, you’re exercising crucial communication skills.

Now, you could just blast off an email, internal survey, or update a wiki page and consider your work done. However, you’re missing out on crucial relationship building and major learning opportunities. Every moment of contact with another team in your company is a leadership and learning opportunity for product managers.

The Secret, Winning Habit of Great PMs

When you’re a product manager you have to influence people, because you have limited power on your own. You need to get buy in to accomplish anything.

And to be a product manager people enjoy working with instead of loathe, you want to be a trusted, respected colleague, not a politician or Machiavellian monster.

And the best way to build that trust and respect? Peer 1 on 1s.

What’s a Peer 1 on 1?

Peer 1 on 1s are a secret weapon for many great companies. They help fellow managers commiserate and support one another, and teams that interact regularly work together better. Usually, these meetings happen every 4-12 weeks, depending on what the two people involved feel is the best frequency.

As a product manager, having semi-regular check-ins with key members of teams you work or interact with can be priceless. It gives you a chance to give and receive feedback, hear new perspectives, gather customer data from new sources, answer product questions, and build rapport with them.

It can also ensure that people understand how you approach product decisions. You may be crushing it as a PM, but that doesn’t mean everyone else sees it that way. Product people have some of the greatest visibility across an organization, which can make it easy to forget that not everyone knows everything you do.

Who should product managers have peer 1 on 1s with?

The culture of your company and the nature of your product can make this vary, so use your best judgment when you apply this to your job.  For me, I was leading product at a 20-30 person SaaS startup, and so I will share what I found worked there based on the advice I received.

1) Your Product Team

Your engineers have an entire engineering org that decides their compensation, job title, and work. All you can do is influence what is worked on next and collaborate with them on making the best (not just good enough) solution. The same goes for designers.

When your team is small, meeting once every month or two with everyone can help ensure you stay on the same page and fix problems. Identifying a bottleneck, something frustrating, or a blind spot can save your team hours, days, or even weeks of lost time from infighting, inefficiency, or poor decisions.

You may also find opportunities to help them understand how you make decisions. This can reduce resistance to changes you propose and open up constructive feedback to communicating with them and their colleagues.

Everyone?!? At first, yes.

When you’re small (7 or fewer designers + engineers), meeting with each person can ensure your processes are working well and ensure everyone feels heard.

As you grow, focusing on the team leads who you work with most can help you scale. They can be a voice for their team. Assuming the design and engineering team leads have one on ones with their teams, they can raise with you any concerns they hear from their teams. (Note: it can help to remind the lead in advance to ask their team before you meet.)

Peer one on ones are a great way to take the temperature of your product team. If when you meet with them, they clam up, refuse the meeting, or seem combative, that’s a major signal you have work to do to improve your teamwork.

Having a good relationship with the product teams you work with is table stakes as a Product Manager. Yet, many PMs mess this up. Good peer one on ones are a good option to improve the relationships no matter your situation with your team.

2) Customer Facing Departments

As a PM, one of your most important jobs is to understand your customer better than anyone. There are only so many hours in the day, so even if you’re awesome and talk to multiple customers every day, you should still look for ways to get additional perspectives. And the best place to get those are others at your company.

Ask yourself: who else regularly interacts with customers?

  1. Customer Success / Support
  2. Sales
  3. Account management

In many orgs those three departments are off in a different area of the company reporting to a different C Level leader than you. They may literally be on a different floor or in an entirely different office. Because of this, it’s easy for sales and product to develop different cultures and even some animosity.

Break down the silos with communication.

Product managers are the perfect people to break down those barriers. You’re probably already working with them more than you realize.

Product people often get pulled into sales calls on the biggest deals, and help launch new features that success teams must document and support. They’re also driving the roadmap that ambitious sales people may use to excite prospects.

When I was running product at KISSmetrics I met with all those groups. And in each case I had two goals:

  1. Find out any lessons I should take back to the product team about customers.
  2. Answer their questions and concerns they have about product today and in the future.

So I set up regular peer 1 on 1s with people from sales, customers success, and account management.

Here’s some of the kinds of questions I’d ask to make the most of the meetings:

Customer Success / Support:

  • What are you sick of answering over and over for customers?
  • What bugs do you find you have to help users work around most often?
  • How can I make your life easier when we launch new features or make changes in the product?

These questions help improve our process around launching new features, updating FAQs, and identifying existing problems in the product we should fix. Few things make success team members stuck on the hamster wheel of never ending tickets feel better than having things that drive them crazy in the product fixed.

Sales:

  • What are common product-related issues that are causing us to lose deals?
  • What features get leads most excited about our product?
  • Are there any areas of the product that are unclear to you that I can help you understand better or fall flat in your demos?

These questions often required me to do a little 5 why’s to dig deeper to really understand and get them out of their sales mindset. Yet, with a little effort, I often found gold when I did. It also helped me better understand how my conversations with customers compared to those by sales. There’s a lot of great customer problem knowledge trapped in your head as a PM. Transferring it to sales team members can drive revenue for your company.

Account Management:

  • What features do you find you have to explain to customers the most? What’s most confusing?
  • Where in onboarding do users tend to get stuck most? How do you help them?
  • What could product do to make your job easier/better?

The people that help customers get activated will know many of the pain points that are affecting your onboarding funnel. Much like Customer Success team members, removing friction they deal with every day can really make their day, and help your customers.

Peer 1 on 1s are a privilege, not a right.

I worked hard to ask lots of questions and be helpful in these meetings. After the first meeting, I expected they would be prepared as well. I only continued meeting with people that truly brought good data, ideas, and/or concrete feedback. Otherwise the 30-60 minutes we would meet could be better spent elsewhere.

This was a challenge, especially in sales. Not all sales people really get to know their customers, but the best ones did. The best could coherently explain why we lost a deal versus just trying to ask me for every feature a competitor had.

The same was sometimes true in success; I didn’t want to know what happened that they remembered today. I wanted numbers so I knew how big a problem it was.

This then helped me make the business case when trying to decide between building something new we could sell and fixing what we had. When you can prove someone that costs $35 per hour is wasting 10 hours a week on something and it affects customers X, Y, and Z, it’s much easier to justify a change.

Build a Customer Driven Culture

When I set out to have these meetings, I was just trying to get more data and feedback to do my job as a PM better. A great byproduct of the meetings ended up being that everyone in the company became more customer driven.

As I met with people more regularly, and they saw me take action on their feedback, it created a positive feedback loop. The more I listened and demonstrated I heard them, the more they wanted to provide more valuable insights and contribute. That led to more discussions about approaches they could use in their job to get me better data and good questions to ask customers.

Patterns converge

What was particularly fascinating to me was that quite often, I would hear similar things from the majority of people I would talk to; often an issue in product would impact everyone in different ways, whether it made a sale harder, increased support tickets, or changed how account managers taught our product.

By empowering all of them to share with me what they were experiencing and teaching them how to best do so, they helped me better triangulate customer needs and calculate fully their impact. With everything else on everyone’s plates, this would never have happened without regularly scheduled meetings to talk about it.

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There’s always more work to be done than time for a product manager. Taking the time to have peer 1 on 1s with key members of teams you work with can be an invaluable part of your processes as a product leader.

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Want to work with a product person that lives this customer driven approach every day?

If you’re an engineer in San Francisco interested in joining a fast growing, early stage startup, I’d love to talk to you about how my startup, Lighthouse, can be a great opportunity for you. Send me an email at jason at getlighthouse dot com and tell me a bit about yourself.

Why don’t we reward good managers?

18 July 2014

{Note: My startup, Lighthouse, just launched its blog. If you’ve been enjoying my posts on leadership and management, follow me over to http://GetLighthouse.com/Blog and subscribe on the right sidebar to get every post.

Below is an excerpt from the first post there, “Why don’t we reward good managers?“}

We all know management is important, and yet, it has not changed the largely dismal outlook of management: 70% of American workers are disengaged. Poor management is largely to blame.

People don’t leave companies, they leave bad managers.

As I’ve spoken to managers and employees, it’s amazing how often I hear about managers that ignore their people, stifle their team’s efforts, and are totally unaware of the unhappiness of their employees. Unfortunately, this candor on their frustration is with me, not their employer.

Some of these issues can come up in 1 on 1s, if you have them often enough and you ask (many are afraid to volunteer such issues, especially introverts). If you miss those opportunities and they’re now leaving, you can do exit interviews to learn what went wrong, but that’s too late to help them. You are also unlikely to get straight answers in an exit interview; if an employee desires to leave on good terms, they have incentive to sugar coat things and find the most diplomatic reason to say they’re leaving.

Bad managers affect everyone.

Good employees work hard to produce, but they resent their manager if they’re not appreciated and treated well. When it happens to mediocre and bad employees, they will just shut down and under produce, creating dead weight on teams. Your good team members will eventually decide they’ve had enough and look elsewhere. In a competitive market, this will happen sooner than later.

Continue reading on the Lighthouse blog…

Why you should think of your employees as Allies in the future of work

8 July 2014

The rules of work have changed. Gone are the days where you spend your whole career at one company that gives you a great pension and a retirement party.  And yet, we still act like that’s the case when we hire people, and in how we approach managing them.

We live in the world of “at will” employment. Layoffs and “it’s just not working out” discussions are always just around the corner.  Meanwhile, many employees job hop from company to company always searching for greener grass.

When talking to candidates, we interview them expecting to hear how committed they are to anything the company wants, even though both sides know a lifetime commitment is pure fantasy.

Why are we lying to ourselves?

Rather than be in denial, we should accept the new rules and take full advantage of them. That’s what Reid Hoffman, Ben Casnocha and Chris Yeh advocate for in their new book, The Alliance I just read.

The current system is bad for everyone. The-Alliance-Managing-Talent-in-the-Networked-Age

It creates major problems for both the company replacing team members regularly and the former employees who see their tenures cut short.

The worst parts about replacing team members are:

  • They leave when you don’t expect it.
  • You have no plan for what to do without them.
  • Work is left incomplete even if they give some notice.
  • Their knowledge and experience is lost from the company.

And for the employee, the worst parts are:

  • Unfinished work and incomplete milestones that now can’t be put on their resume.
  • Less development in their career as companies fear to invest in them.
  • Damaged relationships due to resentment over the first 2 items.
  • Distrust in every employer they have going forward.

Hoffman, Casnocha, and Yeh advocate for a new system that considers employment as an Alliance: a mutually beneficial relationship, without the empty promises of long term employment.

Why You Should Think of Your Employees as Allies in the Future of Work

In an alliance, both sides work together for mutual benefit. This means shifting your thinking on employees. It’s a lot more than, “do this work and I pay you.” Instead, the relationship is, “I help you grow, learn, and tackle these challenges, and the company benefits from that work.”

The authors call this a Tour of Duty. You select a length of time (a year or two up through 5+ years) and a set of goals for them to achieve with core responsibilities. The agreement is that you will help them have a Tour that is of interest and value to them, and they will do good work for your company.

By agreeing on the time frame and what the Tour entails, you eliminate many of the biggest problems for both sides:

  • Employees now have a clear set of goals and milestones and a plan to get there.
  • Employers have more certainty how long they can count on having an employee.
  • Employees have a clear point where they can cleanly transition out if they want.
  • Employers can plan ahead as a tour is about to complete, avoiding any surprises.
  • Both sides have more certainty and a clear commitment to one another.

Now the end of a Tour is not the end of someone’s employment. What Reid Hoffman found with Linkedin, was that people were often hungry for new Tours. It provided opportunities to quickly progress people onto tracks for major leadership roles (they call them Foundational Tours), or give them a new, interesting, challenging job different than what they just completed.

Either way, you can keep renewing the Tours as long as there’s a good fit between company needs and employee interests. And if there’s not a clear fit at the end of a tour, you can have a very smooth transition for both sides, allowing the employee to find work elsewhere without hurting the company or vice versa.

Your people want tours. You just don’t know it.

As I’ve been working on my app for managers, I’ve spoken to a lot of employees in addition to managers. What I keep hearing over and over again is how frustrated people get over a lack of progress in their work.

Employees want to grow and learn new things. They want to be challenged. They want to be recognized for their good work, and feel like they’re working towards something greater than just a list of tasks for the day. When they don’t feel that progress, they feel stifled and quickly lose motivation. Not long after, they’re looking for the door.

Tours address all of these issues. A Tour:

  • Creates a clear set of goals to achieve in a role.
  • Creates a set end point where new opportunities can be explored.
  • Ensures a discussion about an employee’s goals and how they fit into the company.
  • Necessitates regular check ins to be sure progress is made on a Tour and will be completed on schedule.

Planning Tours take effort and have big payoffs.

Planning Tours for your team members doesn’t happen by accident. It’s why they wrote the book and are building a site around the idea (www.theAllianceFramework.com).

You have to have healthy discussions with each team member and plan out a path for them. What can they achieve in a few years? How does that align with their long term goals? What are the measures of success for a Tour for them? Do those goals interest them? If those are questions that are foreign to you, you need to start discussing them.

The best time to have these discussions is during your 1 on 1s.

With so much work to do, so many short term priorities to address, who has time for this? But if you want to keep your best people motivated and engaged and level up your team as a whole, you need to make time for these discussions. That leaves 1 on 1s as your best chance to have the time (You are having 1 on 1s, right?).

You’re already hopefully having candid conversations in 1 on 1s, so it’s time to shift part of each 1 on 1 to work on aligning their long term goals with their current roles and responsibilities. It won’t happen all in one meeting, but you can slowly put together a plan over a series of meetings.

You’ll see the benefits quickly.

Once you start this process, pay attention. Watch closely. The more you align someone’s work with their goals the more motivated they will be. Show them how the work you’re asking them to do gets them closer to what they want and they’ll work harder to help you with what you need.

It’s no mistake. It’s the Alliance at work. As Hoffman, Casnocha, and Yeh, write,

“Every employee relationship should be bidirectional in nature; it should be clear how the employee benefits and how the employer benefits.”

That’s because it creates the best situation for productive, happy work. And the Tour takes that to its greatest outcome by sustaining that over a multi-year period.

Are you creating aligned work for your team? Are you engaging your team towards mutual benefit? If not, learn more in The Alliance and start doing Tours at your company.

Get LighthouseLooking for a system to track your team’s long term goals and break them down into the near term goals you need?

Want to have more effective 1 on 1s that build towards alignment like what’s described in the Alliance?

Then sign up for Lighthouse, the app for managers.

Why Replacing a Good Employee Will Cost you $65,510

2 July 2014

2 Comments

“Oh no! I didn’t know you were leaving, too.”

When a friend left his job, his coworker made the surprise comment that he was about to leave the company as well. What seemed like a few minor problems on the team soon snowballed into a costly mass exodus.

Employee retention is one of the most overlooked aspects of managing your team…right until you start losing good employees. It costs much more than you might expect to replace them. I was curious myself just how much it could cost and the surprising results are below.

Note: All salaries are assumed to be $100,000, which is $40/hr assuming you work 50 hours a week for 50 weeks a year. Adjust the numbers accordingly if anyone costs more or less for you.

The Costs of Sourcing a Hire:

Unless you’re a really hot company, it’s unlikely that great people are beating down your door to fill open roles. And even if you are well known, the best people probably aren’t refreshing your jobs page for an opening. You have to go find them.

You can source candidates a ton of different ways, but they all cost money either in the form of payment to another company or in time invested by one of your employees.

Sourcing CostsWith just a few attempts at sourcing some good hires, between third party costs and labor in your company, sourcing costs can easily reach over $26,000. The scariest thing is, you haven’t even interviewed any of these candidates yet!

The Costs of Interviewing a Hire:

Now that you have a full funnel of candidates kickstarted, you start the dreaded interview process. You’ve got to filter through all the LinkedIn profiles, social accounts, resumes, and cover letters to find those gems who will then navigate your hiring process.

Here the costs are a bit more hidden. It’s all about lost time for various team members. What other great work could your team be doing instead of working on candidate hiring? Every minute spent hiring is a lost dollar invested in your business.

Assuming you have a clear funnel where you only have to look at 120 resumes, only have a third of them make a phone screen, a quarter of those make it to in person interviews, and you prep 3 offers, interviewing costs you over $5,000. For some specialized roles it could be significantly higher if you have many more interviews and phone screens.

The Cost of Onboarding a New Hire:

Congratulations! You found the candidate you’ve been looking for. Now you need to onboard them so they become a productive, integrated member of your team. Again, you have hidden costs. Now, you have losses both in how productive a new hire is versus a veteran on your team, and your team training them (an important investment, but also a significant time sink for your team).

When you hire an employee, there’s often some kind of bonus you need to give them. It might be a salary bump, moving costs, or something else to sweeten the offer. It’s part of the cost of doing business. When you combine that with your costs as they start on your team and get up to speed, onboarding can cost you over $10,000.

Of course, we’re assuming your hire works out, which unfortunately, it won’t always. You can go ahead and double these costs and many of the ones in earlier sections if you have to go back to the drawing board on another candidate.

The Cost of Lost Productivity:

While your team member has departed, the show must go on. The rest of your team has to cover for them, whether that means writing their code, calling their leads, or finishing their reports. As much as you’d like to think the rest of the team can just make up for them, if the hire really was good, that’s impossible. Lost ProductivityWhen someone leaves, team members are distracted. Those that were close to them in particular will be less focused and productive. They’ll probably grab beers with their friend before they leave, when they otherwise may have worked late.

Meanwhile, if you push your team to cover for them, the stress and extra hours can affect their physical and mental health, which will lead to vacation and sick days. If hiring drags on, you’ll probably hire a consultant or freelancer to cover which could easily exceed $100 an hour for their work.

All of this combines to lead to a Productivity loss cost of over $24,000.

So let’s add this up…

Total Costs

Ouch! Replacing even a single team member is expensive! Wouldn’t it be a lot cheaper to retain all your good people?

What can you do?

Next time a good employee asks for a raise, investment in equipment to help them on their job, or a morale boosting opportunity is presented, consider the cost of losing them before saying, “we have no budget for this.”

If your manager is blocking you from helping your team, remind them what you’re asking for is a lot less than the $65,000 cost to replace a lost member of your team (let alone the cost of multiple losses!).

While free lunches, ping pong tables, extra vacation days, and other perks are a nice bonus, they aren’t what keep people at a company. Even raises only satisfy people for a short period of time.

What really retains teams is managing people well.

This comes by having discussions with them about their personal growth & goals, company and self-improvement, and recognizing the things that are important to them personally.

I know that’s easier said then done. You have a million things on your plate as a leader and what little time you can spare has to be maximized. And it probably isn’t right now.

You have notes on people all over the place. One on ones are sporadically effective, because you may not always be prepared for the next one. Goals are a great idea in theory, but they’re buried in your HR app you can’t stand.  There must be a better way.

Get LighthouseThat’s why I started Lighthouse. It helps you stay on top of what matters quickly and efficiently for each of your people. It’s designed with managers like you in mind, because I’m a manager myself.

If you want to be the manager people love to work for & save the costs of replacing people, sign up at GetLighthouse.com.

What to Expect When You Start Having 1 on 1s

27 June 2014

2 Comments

Ben Horowitz advocates for 1 on 1s. So does Marc Benioff, the team at Bufferapp, and many, many others. Yet, in many ways they’re still shrouded in mystery.

Some people see them as a waste of time. Others are unsure how to make the most of them. Ask 10 managers and you very well could get 10 different answers.

If you’re convinced to get started with 1 on 1s, and never done them before, you’re in for a few surprises. Here’s a few tips for what your should expect:

1) They are different than any other meeting

As a manager and leader, you’re in a lot of meetings. Probably more than you should. And in most of them you’re being asked to give your opinion, make decisions, and answer questions that all focus on driving the business forward. One on ones are nothing like that.

As Ben Horowitz suggests after he took some heat for his firm stance on the importance of having 1 on 1s,

“The key to a good one-on-one meeting is the understanding that it is the employee’s meeting rather than the manager’s meeting. This is the free-form meeting for all the pressing issues, brilliant ideas and chronic frustrations that do not fit neatly into status reports, email and other less personal and intimate mechanisms.”

It bears repeating: One on ones are all about the team member, not you nor the company. You need to flip your mindset to thinking about what’s important to them and how you can help. This context switch can be difficult, but the payoff is huge. Set the standard that you recognize that these meetings are different from other meetings and you’ll be on your way.

2) You will learn important things you won’t hear any other way

You may think you know your team really well. You may think you know everything they’re thinking about for work and have addressed all their concerns they’ve aired publicly. If you’ve put in some effort to listen to your team in a group setting, that’s a great start, but there is always more they’ll bring up privately in 1 on 1s.

As URX CEO John Milinovich recently said in his interview with First Round Capital,

“There will always be things that people won’t bring up in a community forum that are still so important to address, especially before they become bigger issues.”

Build a trusting environment in your one on ones and follow through on what you hear and you’ll be amazed at what you’ll learn people are thinking about or have concerns with. The more you act on what they confide in you, the more they’ll share that will improve the company, your team, your management, and them as an employee. For the introverts on your team, who are less likely to bring up any issues publicly, this will be especially important.

3) They should bring things to talk about, and so should you.

It’s easy to put the obligation on your team member to drive the 1 on 1. It’s definitely important to let them talk about things that are important to them. However, especially early on, you need to bring some questions as well.  There’s a ton of different 1 on 1 questions you can rotate through and you can also use 1 on 1s as great coaching opportunities.

As Jason Lemkin (CEO EchoSign, VC @ Storm Ventures) writes,

“You may think you know if you have drinks together, or go see movies together, or whatever…But you don’t.  Even if people complain in that context, it will be general complaints.  You won’t learn what your top people need to find their growth path at your company.  Where they feel stalled out and frustrated.  You have to ask.“

By mixing up the questions you ask, you will ensure you’re not missing anything they may be afraid to bring up.  You’ll also avoid 1 on 1s getting into a rut where certain topics become safe and easy, at the expense of never discussing any elephants in the room. You get out what you put into your 1 on 1s, so prepare, listen carefully, and follow through.

4) They may be a little awkward at first

Your first one on one won’t be easy. It can be especially awkward if you recently got promoted and now you’re having a one on one with a former peer. Fight through the ‘fight or flight’ urge to not ask the questions a manager should ask in a one on one. Those early questions will break the ice and give you your first opportunities to build deeper trust and rapport with them. Over time, you’ll get in a rhythm and build trust. Then you’ll probably even look forward to them.

Stick with them. The benefits are huge as Michael Wolfe (PipeDrive, Vontu, Kana) wrote,

“Over time you can build up a very good relationship with most people simply through this time investment. Even though you may need to discuss tough issues, try to build up enough trust and openness between you that you can enjoy solving problems and working to make the company better.”

It’s a relief when a problem at work is solved. If you form a real partnership with your team member to address the issues they bring up, they’ll trust and respect you more even if you don’t always give them the answer they want to hear.

5) You will quickly learn why this is a manager’s best tool.

The conversations in one on ones are the keys to understanding your people and motivating them.  Everyone has different drivers and idiosyncrasies; the better you understand them, the more effective you’ll be able to work with them.

As Ben Horowitz notoriously recalls when he almost fired two people over a manager not having one on ones,

“Being a good company doesn’t matter when things go well, but it can be the difference between life and death when things go wrong…and things always go wrong.”

Unfortunately, if you don’t do one on ones, Ben continued,

“…there is no possible way for him to even be informed as to whether or not his organization is good or bad.”

You can fix so many problems and improve the morale of everyone on your team with these meetings. You’ll find out about issues before they blow up. You’ll be able to help people when they’re struggling, and give them good and bad feedback regularly.  You can talk about career goals and growth opportunities regularly. Bit by bit you’ll see improvements across your company and you’ll wonder why you didn’t do them sooner.

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black_alphaWant help getting started with one on ones? Want to build a better relationship with your team members?

Lighthouse keeps you organized and prepared for everything that matters to your team members including goals and 1 on 1s. Learn more at GetLighthouse.com

Do You Believe in Your Team?

20 June 2014

Whether you’re young or old, we all have dreams and aspirations. If you can help someone uncover those goals, then encourage them, and tell them you believe they can do it, you will truly inspire them. As a manager, believing in who your people can become is the most powerful thing you can do.

Think back. When was the last time someone believed in you? When did someone give you a task that pushed you beyond what you’ve already done? When did you last hear, “I know this is a big challenge for you, but I believe you can do it and I’m here to help.”

If you haven’t heard it, I’m sorry. Do it for someone else and see how they light up. If it’s something they truly aspire to, you will see some of the best work you’ve ever seen from them (and for *all* their work, not just related to their goal). They’ll also be very receptive to your feedback and guidance.

I have been endlessly amazed with what members of my Greenhorn Connect team have been able to do over the years because I’ve believed in Paul, Pardees, Angela, Ariel, and others. I saw them for more than the inexperienced members of the startup community they were when each of them joined the team.

Instead, I focused on the skills they could build on and listened to what they said they wanted to become. Greenhorn Connect would not be what it is today without them rising to the occasion in each of their roles, especially since I moved thousands of miles away from the business 2 years ago. And it all started with believing in them.

See more in people.

Ford’s quote is true for you, and it’s true for your team. Don’t waste your team’s careers only doing what they’ve always done. Uncover their aspirations and find a way to make your company or your department a conduit for them to achieve their goals. Even if they outgrow their role, the quality of work you will get before they do so will astound you.

Life is too short to be boxed in by what you’ve already done. Be the one person that sets them free to grow and you will have a friend and ally for life.  This is why the best leaders have people that work for them again and again. It’s not because they like the box their leader puts them in; it’s because that leader helps them truly reach their full potential.

How can you do this?

It starts today. You should be regularly discussing your team member’s goals and the work they’re doing. No other forum is as helpful as leveraging 1 on 1s for this.  In those 1 on 1s, you can discuss their progress, coaching, and learning opportunities. You can also keep a pulse on what they really want, as it will change over time.

Take time and reflect on each person as you prep for their 1 on 1. What are their strengths? How can you help them grow in their role? Progress is the spark for the fire of motivation for each of your team members. Help them feel that progress in their role.

As your team grows, keeping track of all of this can be a struggle. It’s not that you don’t care; it’s that the demands of your job only give you so much time.

Get LighthouseTo make the most of the time you do have, track everything and stay organized with Lighthouse.

I’ve built it to help myself as a manager, and it will help you make the most of every 1 on 1 so you have an excited, engaged, team you believe in.

Sign up and learn more about being a better manager at GetLighthouse.com

10 Common Ways to Lose Good Employees

11 June 2014

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“I’m leaving. My last day is next Friday.”

I still remember the surprise when one of my old coworkers announced that to the company. He was one of the longest tenured members of the team and seemed content on the job. Little did I know he had a number of motivations for wanting to make a change that may have been avoidable.

The competition for talent is always high, and especially now you can’t afford to lose a good employee. Even the most loyal members of your team have breaking points that will make them want to look for a new job. And worst of all, when employees leave, it often happens in waves, meaning that you lose more than just one person at a time.

People leave bad managers, not jobs, which means as a manager, you have the power to prevent many of these losses to your team. Avoiding these pitfalls will put you well on your way to retaining your team.

Commons Ways to Lose Good Employees

1) Don’t Follow Through

I’ve written about this a number of times before and it bears repeating: not following through with commitments to your team will quickly build resentment. That resentment will lead to complaining amongst team members behind your back and a lot of frustration and distrust that can hamstring your team’s productivity.

What to do instead: Use a to do list or other system to track your commitments to your team to make sure nothing slips. If there’s something that prevents you from following through that’s beyond your control, be transparent with your team and help them understand why you couldn’t do it.

2) Don’t have 1 on 1s with them

If you’re not having 1 on 1s with your team, you don’t know what they’re really thinking. 1 on 1s are a huge opportunity to have a private line of communication with each of your reports. You can learn tons of different things based on the questions you ask in a 1 on 1, and fix a lot of problems before they blow up. There’s a reason Ben Horowitz was willing to fire a manager for not having 1 on 1s.

What to do instead: You may think you don’t have time to have 1 on 1s, but what you really don’t have time for is to lose your best people and have to go through the hiring process and covering for lost staff again. Get started having 1 on 1s at least once a month (ideally more) and use an app like Lighthouse to help you stay on top of them.

3) Ignore Their Ideas

Are your employees trying to tell you something? Do they see a problem you don’t? Do they have ideas to improve the way they work or a system around them? This is a gold mine of ways to make your company better and make your team happier. Yet, many ignore this and see people instead get frustrated by a lack of change in areas they think are important.

What to do instead: Use part of your 1 on 1 time to ask questions about ideas they have to improve the company, the team, and their own work environment. Take action when you can on those suggestions and explain why some things may not be possible right now.

4) Don’t Treat Them Like Adults

Do you trust your team? If you can’t trust them you may not have the right team. Good people, especially those with long tenures, expect some transparency into what is going on outside of the team. They also want to be trusted with their work instead of being micromanaged.

What to do instead: Trust, but verify. Give people the independence to do their job, but hold them accountable to the results you agreed upon. Trust them with information they want to know and make sure they’re keeping anything private you asked them to.

5) Under Compensate Them

Are you paying anyone well below market rate? Have some of your team grown in their roles and are now significantly outperforming their compensation? Have you moved a team member to a more expensive city without properly increasing their salary for cost of living? Any of these, as well as disparities in equity can lead to a lot of resentment. It can also tempt people to see what they’re worth elsewhere and by the time they have an offer, it’s too late.

What to do instead: Plan ahead for managing people’s compensation, especially for people taking on more responsibility. Your budget may be tight, but if you make incremental improvements you won’t wake up a few years down the line searching for a massive amount of money to adjust someone’s salary who has one foot out the door.

6) Don’t Praise, Recognize or Reward Good Work

Do you reinforce the good work done by your team? Do you tell them specifically why the work was great? If you don’t recognize good work, your team will not be as motivated to repeat those efforts again.  Mary Kay Ash, of the founder of Mary Kay cosmetics, put it best when she said:

“There are 2 things people want more than sex and money: recognition & praise.”          – Mary Kay Ash

What to do instead:  Take time to recognize people for great work. If it’s really awesome, recognize it in front of their peers. Also give them specific reinforcement over email and in 1 on 1s. As long as you are specific why you’re giving them praise, it will be well received.

7) Keep Bad Employees

Nothing frustrates good employees like working with bad ones. Bad team members make it harder for everyone else to get their work done, slow down progress, and lower the bar for the quality of work a team outputs. Bad team members can quickly turn a strong work environment into a toxic one either by their own work or due to how the team reacts negatively to them.

What to do instead: If you can, fire them. Your team will breathe a sigh of relief and you’ll find your team is more productive without them. If you can’t fire them, try to minimize how they impact others by putting them on work that they don’t affect as many people on the team.

8) Don’t Align Their Work with Their Goals

Do you know what the goals of your team members are? Does their work put them in line to accomplish those goals? Are they growing? If an employee isn’t achieving their goals, they will feel stifled and likely grow bored with their job. When a person’s job doesn’t help them achieve their goals, they’ll be motivated to look elsewhere to reach them.

What to do instead: Have conversations about goals in your 1 on 1s. Work to align parts of their job with these goals and make them feel like there’s a plan to help them achieve them over time. Apps like Lighthouse can help you manage and remember these.

9) Embarrass Them in Front of Their Peers

This may seem like an obvious one you would never do nor allow in your company, but it might have happened without you realizing. Ever casually call someone out across the office over a mistake or to make a joke?

I had a boss who wanted to prove that everyone (except me) cheated in school and proceeded to try to ask everyone around the office if they cheated. I think it was meant to be funny, but I remember how uncomfortable I felt then. Whatever it is, it can seem innocent, but even things you think are light-hearted can hurt people no matter what face they put on publicly.

What to do instead: Don’t be the one to do these sorts of things and shut down anyone you see doing it as well. If you’re treating your team like adults, then embarrassing peers is a childish behavior you should not tolerate. If it does happen, apologize and make sure it doesn’t happen again.

10) Don’t Help Them Make Progress Regularly

The feeling of progress is crucial to people’s satisfaction. They need to feel like they’re progressing on their work and that their work matters to the company’s bigger picture. When people aren’t making progress, they start to burn out. Nothing is more devastating to a great employee than burn out. It saps them of their abilities to be a productive, skilled team member.

What to do instead: Make sure team members have projects that are broken into small enough chunks that they can regularly make progress on them. Check in with them on their goals to make sure they’re making progress on them. Read more about progress on teams here.

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These are all hard lessons to learn, but the good news is that usually people leave for more than one reason. That means an occasional slip up will be forgiven, while breaking many of these will have your team looking elsewhere for work.

What are the behaviors you’ve seen cause good people to leave?

Get LighthouseWant help keeping your team motivated and turning down recruiting emails from friends and recruiters? Lighthouse was designed from the ground up with a workflow to help you follow the best practices of great managers.

Learn more and sign up at GetLighthouse.com

10 Critical Mistakes You Could Be Making in Your 1 on 1s

5 June 2014

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One on ones are a crucial part of good management practices, but just because you have regular one on ones with your team doesn’t mean you’re making the most of them. You could even be doing serious damage to your relationship with your team if you don’t do them correctly.

As a manager, your job is to amplify your team to allow them all to perform more efficiently and effectively. Your 1 on 1s with them are your best weapon to raise performance and address issues. However, making these crucial mistakes below can damage your relationship with your employee and prevent you from discovering the kinds of things that will fix problems, raise morale, and motivate team members. Hopefully you aren’t doing many of them, but if you are, there’s no time like the present to turn it all around.

Critical Mistakes You Could Be Making in 1 on 1s

1) Not following through

If you’re talking about ideas, problems, or things important to your report in your one on one, but then nothing is ever done about what you talk about, you’re making a lethal mistake. The effectiveness of one on ones is based on trust, and that comes from following up and following through on what you discuss.

When you lose the trust of your report, they will shut you out and won’t share feedback, ideas, or problems with you. They will feel there is no reason to waste effort talking about things that will never happen and they’ll resent you for it. This is the path straight to losing a team member.

What to do about it: End your one on ones by specifically setting what you and your report’s tasks are because of what you have discussed in the meeting. When you take action on something important they brought up, let them know and thank them for bringing it up.

2) Canceling one on ones

One on ones are the one meeting your report has that’s all about them. The rest are all about what the company wants and needs. When you cancel their one on one, you may think it’s ok, and they’ll probably even say it’s ok if you ask, but it’s not. They will resent you for not treating the conversation about them as important.

It will also break your rhythm of these meetings regularly covering important topics and addressing them; if you go a month without having a one on one, so much may build up that you’ll miss covering something important.

What to do about it: Book your one on ones on your calendar for a consistent time you know you can stick to. If you absolutely can’t make a one on one, then reschedule it for as soon as you can after the cancellation rather than not having it at all.

3) Turning them into status updates

One of the most common things I’ve heard as I talk to people about management is how often a significant portion of the meeting is spent giving a status update of their projects. Nobody wants to have more meetings than necessary, but by putting a status update into a one on one, you’re squeezing time spent on the most important subject of one on ones: your team member.

What to do about it: Have a separate meeting to do status updates or consider using an app like idonethis to stay up to date on what people are accomplishing without having to talk about it in one on ones.

4) Not preparing

Yes, one on ones are all about your report. And yes, they should be bringing things to talk about in the meeting. However, assuming you don’t need to prepare at all for the discussion is a big mistake. Context switching to the meeting can be difficult if you’ve been working on other things and like it or not, your report can tell when you’re really ready for the meeting. Not preparing also makes you miss out on great coaching and feedback opportunities.

What to do about it: Save a few notes and to do items from each meeting. Review them before your next meeting and bring a couple questions for the one on one with you.

5) Not talking about their goals

It’s easy to spend all your time focused on short term issues in your one on ones, but what will make people happiest is when they’re making progress on their long term goals while working at your company. You are unlikely to find out what those goals are unless you talk about them and there is no other time as ideal as the privacy of a one on one to explore their big life goals.

What to do about it: Every month or two, revisit questions about their goals and what you can do to help them make progress on them.  Keep these goals written somewhere you can easily reference, like Lighthouse, so you can take action on them when opportunities arise.

6) Not asking tough questions

It’s easy to get into a rut with one on ones and thus only cover a fraction of the topics that you could. Your one on one time is an amazing opportunity to get insights on many things including: improving the company, feedback on being a better manager for them, feedback and coaching them, improving morale in the company, managing goals and uncovering team issues. Don’t waste it only talking about a fraction of those things.

What to do about it: Rotate through the topics on this list of questions for one on ones and always follow through so your report knows they can really talk to you about anything.

7) Not having them at the right frequency

When someone is brand new to your team, it’s important to have one on ones often so you can build rapport and trust quickly. Also, if every one on one is running long, you may want to have your one on ones more often with them.

On the other hand, if you’re doing them weekly and finding often the meetings aren’t yielding much to talk about even as you cover all the tough questions, then backing off to biweekly or monthly may make sense. This will happen especially with colleagues you’ve worked with or known for a long time.

What to do about it: Challenge yourself to look hard at what’s happening in the one on ones. Are you covering everything you should? Do you know them well enough to detect a problem early without a 1 on 1? If so, you may be able to have them less often. If not, you may want them more often.

8) Not holding them accountable

You’re not having one on ones to play psychologist. You are having them to address issues, understand your team members, and hear what they want. Both of you should have takeaways from each one to make sure you’re both making progress in the areas you agree are important. Letting them slip by with not being actionable in your discussions or not taking care of the action items you discuss, is wasting the time of both of you.

What to do about it: End every one on one by asking them what you can hold them accountable to before your next one on one. Circle back in the next meeting to make sure things are getting done. You should notice an increase in satisfaction that comes with a sense of progress from completing agreed upon takeaways.

9) Not being present in meetings

Have you ever caught yourself zoning out, checking your phone, or looking at email when you’re supposed to be listening to them? Just like canceling a meeting hurts them, not giving them your undivided attention will as well.  You may be able to get away with it in a big meeting (though that’s not good either), but this is a one on one, so you are the center of the other person’s attention. You aren’t as sneaky or as good at multi-tasking as you think.

What to do about it: If your computer in the meeting is too tempting, leave it at your desk. Do the same for your phone if you have to. Many managers use Moleskin notebooks for these meetings since all you can do is jot notes, not the million other distractions we have today. They then transfer them to their note taking app later.

10) Thinking you don’t need a 1 on 1, too

I know. You’re busy, and your manager is even busier. And that’s all the more reason for you to touch base in a 1 on 1 for yourself, too. Some of those subjects you’re covering with your team in their one on ones will need to bubble up to your manager, who can also help you in many of the same ways you have been helping your team.

Just because you’ve gotten a promotion to manager doesn’t mean your career is set. Continuing to learn where you can improve and talking about your goals is all the more important when you are trying to lead a team of others.

What to do about it: Share with your manager the positive results you’re getting from the one on ones you’re having with your team and tell him you want to do the same. Results will grab their attention and convince them of the value.

What mistakes have you made in 1 on 1s? How have you improved them?

Get LighthouseWant to have great 1 on 1s with your team? Lighthouse helps you have great 1 on 1s by helping you follow best practices, always be prepared, and follow through on what you discuss. Your team will love you for it.

Learn more and sign up at GetLighthouse.com

101 Questions to Ask in One on Ones

29 May 2014

3 Comments

So you’re having one on ones with your team. Awesome. It’s an essential element to being a good manager. But are you making the most of them?

Do you come in prepared and ready to make the most of each one or do some go better than others as you wing it half the time? Are you too dependent on them bringing the agenda? Do you ask the same 3-5 questions every time?

This list will help you make the most of each meeting and have a quick reference when you feel your questions may be getting stale or you have a few minutes left in a one on one.

101 Questions to ask in one on ones

One on ones are all about your people and building a strong, trusting relationship with them. Asking questions like the ones below and following through on what you talk about will build a strong, lasting relationship for each member of your team.

Asking 1 or 2 of these questions each one on one will keep things fresh, while ensuring you’re covering important subjects regularly. It also gives you ample time to dive into each question as they often will open up into greater detail as long as you follow up with questions like “Why?” and “Tell me more…”

I’ve organized these questions by the high level categories you’ll commonly touch on in one on ones so you can quickly skim through it for a question in a topic you want to cover that meeting.

Questions to talk about Short Term Goals

Short term goals are things to be done in the current quarter or month. They’re high level projects assigned to that person.

1) How is [project] going? What could we do to make it better?
2) Is there anything blocking you from getting your work done?
3) Are there any projects you’d really like to work on if you were given the opportunity?
4) What parts of your job would you like to deepen your skills in or get additional training in?
5) Is any part of your project unclear or confusing?

These are all about getting feedback so you can improve their day to day and relieve frustrations on their projects. You already spend a lot of time on their day to day job in standups, status reports, etc so this is intentionally a short set of questions relative to other areas you spend a lot less time talking about usually.

Questions to talk about Long Term Goals

Long term goals are all about who they want to become. Everyone is growing in different ways and people are happiest when they feel like they’re making progress on their big life goals. These questions will help you learn what those goals are and see if they feel they’re making progress on them.

6) What do you want to be doing in 5 years? 10 years? 3 years?
7) What are your long term goals? Have you thought about them?
8) Do you feel like you’re making progress on your big goals here? Why or why not?
9) What’s one thing we could do today to help you with your long term goals?
10) Do you feel we’re helping you advance your career at a pace you would like?
11) Who do you really admire? Why? (People often admire those they want to become)
12) If you had millions of dollars, what would you do every day?
13) What are your super powers? What powers would you like to develop?
14) What are your big dreams in life? Are you making progress on them?
15) Could you see yourself making progress on more of your goals here? What would need to change to do so?
16) What work are you doing here that you feel is most in line with your long term goals?
17) As a kid, what did you want to be when you grew up?

These questions will help you make sure your people are progressing in the areas that matter most to them. Realize they will change over time, and it takes time for people to really open up about their dreams, so it helps to revisit them regularly.

Questions to talk about Company Improvement

Company suggestion boxes have a pretty bad reputation for being unread and never acted on. It’s also hard to convey the nuances of a problem or opportunity for a company on a tiny note card or feedback form.

Asking questions about improving the company during one on one time can help uncover what people in the trenches are seeing and get great ideas to improve the company. All of this while having the chance to easily ask follow up questions to better understand them.

18) What is the company not doing today that we should do to better compete in the market?
19) What’s one thing we’d be *crazy* not to do in the next quarter to improve our product?
20) How could we change our team meetings to be more effective?
21) If you were CEO, what’s the first thing you’d change?
22) Do you think our company is loyal to its employees? Why or why not?
23) Are there any aspects of our culture you wish you could change?
24) What are your favorite parts about our culture?
25) Do you feel over-worked, under-worked, or just the right workload?
26) Why do you think [employee who recently quit] left? What did they tell you?
27) What would convince you to leave for a job somewhere else?
28) Which company values do you like the most? Which the least? Why?
29) What is the #1 Problem at our company? Why?
30) Do you feel like you’re on the same page with your team? How often do you think you need meetings to ensure you stay that way?
31) What do you think are the long term prospects of the company?
32) How many hours a day do you feel you’re productive? How could we help you be more productive?
33) How could we be more creative or innovative as a company?

You may not always like the answers you hear when you dig in for feedback like this, but that’s the point. If you take action on the things you can change and help your reports understand why some others are the way they are, you can help relieve a lot of frustration while making people feel heard.

Questions to talk about Self Improvement

Creating a culture of learning and self improvement starts with discussions like one on ones to help people understand what they should do differently. By discussing them in private, you avoid embarrassing them in a more public setting and can coach them through the changes needed.

34) Do you feel challenged at work? Are you learning new things?
35) What area of the company would you like to learn more about?
36) What skills would you like to develop right now?
37) Who in the company would you like to learn from? What do you want to learn?
38) How do you prefer to receive feedback?
39) Do you feel you’re getting enough feedback?
40) What’s a recent situation you wish you handled differently? What would you change?
41) What additional training or education would you like?
42) Are there any roles in the company you’d like to learn more about?
43) What do you think are the key skills for your role? How would you rate yourself for each of them?
44) Is there an aspect of your job you would like more help or coaching?

These questions will all reveal ways you can help people grow and improve them in their job. The key is to realize that the follow up questions need to include action items and advice for helping them make progress on what you just discussed. Doing always trumps just talking about it.

Questions to talk about Manager Improvement

The saying goes, “People don’t leave jobs, they leave managers.” That means receiving and getting feedback from your team members is a crucial part of your job.

Asking your team directly for feedback will help you not only improve, but also build the trust that you’re as open to feedback as you want them to be. Set a good example with questions like these below.

45) What could I do as a manager to make your work easier?
46) What do you like about my management style? What do you dislike?
47) Would you like more or less direction from me on your work?
48) What could I do to make you enjoy your work more?
49) How can I better support you?
50) What would you like to know about me?
51) Is there a situation you’d like my help with?
52) What is something I could do better? What is a criticism you have for me?

When your reports have the courage to give you candid feedback, make sure you fully understand it and thank them. It can be scary to say something negative to their manager. If you don’t follow through on the feedback, you will lose their trust and they may start to resent you.

Questions to talk about Happiness

Whether it’s a work related issue or a personal one, a person’s happiness will have a major impact on their productivity and morale at work.  A one on one is the best time to dig into any issues that may be affecting them and do things to help them with it.

53) Are you happy?
54) Are you happy working here?
55) Are you happy with your recent work? Why or why not?
56) What would make you leave this job for another?
57) What’s one thing we do to help you enjoy your job more?
58) Is your job what you expected when you accepted it?
59) What worries you?
60) What’s on your mind?
61) What’s not fun about working here? What do you enjoy most about working here?
62) Who are you friends with at work? (Shown to be a key to enjoying your job)
63) When was the time you enjoyed working here the most?
64) What do you feel is your greatest accomplishment here?
65) What’s something you feel is undervalued that you contribute to the team?
66) What part of your job do you wish you didn’t have to do?

These can be some of the hardest questions to ask. If someone is unhappy, they can be particularly cagey, so do your best to give them space and listen carefully. Helping them based on these answers can save an employee you were on the brink of losing.

Questions to talk about Personal Life

Your employees are one complete person. No matter how much you’d like them to, problems in their personal life will affect them at work. You don’t need to be there therapist, but a little empathy can go a long way with these kinds of questions.

67) How are you? How is life outside of work?
68) How do you feel your work/life balance is right now?
69) How do you feel about your current compensation (salary and benefits)?
70) What’s one thing we could change about work for you that would improve your personal life?
71) If around a holiday: What did you do for [Holiday]? How was it?
72) How are your parents/grandparents? Where do they live?
73) If they have children: How is [name of child] doing? (Ask something related to their age like starting school, playing sports, or other interests.)
74) What do you like to do in your free time? What are your hobbies?
75) What did you do for fun in the past that you haven’t had as much time for lately?
76) What drives you? What motivates you to come to work each day?

These questions can help you much better understand people’s motivations and interests. Empathizing with situations like a divorce, sick parent or grandparent, a death in the family, or positive moments like children, a successful side project, or fun activity can all go a long way towards building great rapport for your team. It can also inspire inexpensive ways to thank a team member.

Questions to talk about Team Relations

Your team spends 8+ hours a day working together. One of the biggest opportunities for improvement in productivity comes from improving the interpersonal relationships among team members. Questions like these help uncover problems and opportunities to help every person become a better team member.

77) Who on the team do you have the most difficulty working with? Why?
78) How would you describe the work environment on the team? Is it more competitive or collaborative?
79) How could we improve the ways our team works together?
80) Who is kicking ass on the team? What have they done?
81) Who do you admire on the team? Why?
82) Do you feel your ideas are heard by the team and I?
83) Who would you like to work more often with? Why?
84) Is everyone pulling their weight on the team?
85) Do you help other members on the team? Do others help you when you need it?
86) What’s one thing we should change about how our team works together?
87) What characteristics make someone a good fit for our team? How would you look for those characteristics in an interview?
88) What’s the biggest thing you’d like to change about our team?
89) What do you like most about working on our team?
90) Has anyone on the team ever made you feel uncomfortable? What happened?

One on ones are a great time to coach people on issues they’re having with coworkers. You can also use it as an opportunity to uncover problems on the team before they blow up into a big deal.

Questions to talk about Work Habits

The more you can learn and understand how each team member operates, the more productive they can become. These questions can help you work with them to learn what their work habits are.

91) What part of the day do you have the most energy and focus? When do you have the least? What changes could we make to your work schedule to accommodate this?
92) What are 3 things would you buy to improve your productivity if money was no object?
93) What is an ideal, productive day at work for you? Walk me through the day…
94) What’s an inexpensive thing we could do to improve our office environment?
95) What are the biggest time wasters for you each week?
96) What makes you excited and motivated to work on a project?
97) When you get stuck on something, what is your process for getting unstuck? Who do you turn to for help?
98) What part of your work routine do you find is working best? What area do you want to improve?
99) Are there any meetings or discussions you feel you should be a part of that you’re not? Are you included in any you don’t want to be a part of?
100) What do you do when you feel low energy or unmotivated?
101) How can I help…? (be more productive/happier at work/enjoy work more/etc)

The best ideas come from people in the trenches. While you may be in meetings, buzzing around the office or traveling, they likely see things in the office that affect their productivity a lot (for better and worse). Making changes can have a huge impact on your team’s output.

…and the 2 questions to ask in *every* one on one:

None of the things you talk about in one on ones matter if you don’t follow through and take action on them. These two questions will ensure you always follow through with the important things you discuss in your one on ones:

1) What can I hold you accountable for next time we talk?
2) What can I be accountable to you for the next time we talk?

Wow. That was *a lot*!

Shout outs to Popforms, Manager Tools, and this Quora thread for help inspiring this list.

Want to make these part of Your One on Ones?

Get LighthouseYou can get a pair of these questions, as well as a reminder of what you talked about last time, as part of a prep email from Lighthouse, the app to help you be a better manager.

It also helps you manage the actionable questions you should ask at the end of *every* one on one. Learn more and sign up at GetLighthouse.com