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.
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 sideshave 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.
Looking 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?
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.
“If you always do what you’ve always done, you’ll always get what you’ve always got.” – Henry Ford
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.
To 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.
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.
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?
Ben Horowitz, VC and founder of Opsware (sold to HP for $1.6 Billion), said this to one of his reports when he discovered that a manager had not held 1 on 1s with his team members in over 6 months. Horowitz cared so much about a great work environment for his employees that he considered a lack of 1 on 1s a fireable offense for the manager and the manager’s manager.
Crazy? Over the top? Maybe not. Former Intel CEO and legendary author on leadership and management Andy Grove is an advocate for 1 on 1s as well. Many well known companies today including HubSpot, Moz, and Atlassian, use them, too.
And why do they all make 1 on 1s a key part of their management?
1 on 1s are an open line of communication to understand what is on the mind of each of your team members. It helps you get in front of problems before they blow up and it gives your team a recurring way to have their voices heard. It can also save you from having an employee leave the company without warning.
Even if you’ve bought into the importance of 1 on 1s, there’s still the question of how to get started from scratch. It can be intimidating and a little awkward at first, but with the right plan, you will learn invaluable things in the meeting and have much happier employees.
Ready to start your 1 on 1s? Here are some tips I’ve learned along the way from my own mistakes and the advice of more experienced leaders.
3 Keys to Starting 1 on 1s on Your Team
1) Scheduling 1 on 1s
At least 30 minutes, no more than 60 minutes.
– Context switching can be hard for you and your report. Meetings are usually about work issues, so switching to talking about themselves often doesn’t click right away. For this reason 15 minute 1 on 1s are ill-advised, because you’ll just be getting warmed up when it’s over. Shorter 1 on 1s also run the risk of a late start leaving no time for actual discussion. You can always end a meeting early if everything is good, but you want the flexibility to run a little longer if you’re digging into something important.
Always the same time and day.
– You want to get into a rhythm with these meetings. This ensures you have a regular discussion that your team member can count on. It also helps you avoid having to cancel and move them around constantly. Ideally, you’ll pick a time you know you’re more likely to be around and available on a regular basis.
Choose a frequency you can handle.
– Weekly is best, but if you have too many reports for that or know your team very well, every 2 weeks is fine. If you push to a full month between 1 on 1s you may be going too long between discussions. You will know you need to have 1 on 1s more frequently if every 1 on 1 seems to run long or you struggle to dig into issues that are really important to them.
2) Having a Good 1 on 1
This is their time.
– This meeting is not a status report on projects they’re working on. The other 39 hours (or likely really 59 or more for many of you) are all about what you and the company need. 1 on 1s are a time to listen to them and hear them out. The goal is to help them be more happy and productive at work. Set that standard from the very first meeting and you’ll have much more productive 1 on 1s.
Try to get out of the office.
– You want to hear about issues they’re having and talk about their goals and interests. This context switch from getting work done to talking about them can be hard. It can also be uncomfortable to talk about a problem you’re having with a coworker in a conference room near that person. Getting into a different environment, like going for a hike, to a coffee shop, or to grab a beer at a pub, can all help aide that context switch. Bonus points if you can pick a location they particularly like to further reinforce that this is their time.
Have a few questions ready.
– When you first start 1 on 1s, people can be a bit nervous and reserved. Some more introverted employees will always be that way, so start from the first meeting having a few questions ready to ask them to spark conversation. Some good examples of questions include:
How do you feel [current project they’re on] is going? Is anything frustrating you? What are you enjoying about it?
Is anything exciting you at work right now?
What are your long term goals? Do you feel you’re making progress on them? (This is a question that often changes and needs revisited as you build trust.)
Be open and listen. It’s a friendly conversation, not an interrogation. The more they feel heard, the more they’re likely to open up. You won’t get everything in the very first meeting, but over time, you’ll see them trust you more and more as long as you avoid the pitfalls that can ruin 1 on 1s.
3) Avoiding Major Pitfalls
Never Cancel a 1 on 1.
– It may not seem like a big deal to you, but it really hurts your team member when you cancel a 1 on 1 with them. In their view, you’re saying, “this meeting isn’t important to me,” which then says to them they aren’t important to you. This is why scheduling the meetings at a recurring time you can stick to is so important. If you absolutely can’t make a 1 on 1, realize that rescheduling is much better than flat out canceling.
Always follow through.
– If you talk about problems they have, but never do anything about them, you’ll only further frustrate your team members. They’ll then shut you out and won’t give you feedback any more. The benefits of 1 on 1s will be lost. Instead, make sure you follow through and follow up with them on the issues they raise. That feeling of progress is what will build trust to discuss more things openly with you. It will also act as a pressure release valve on issues that may otherwise lead to major problems or them getting upset enough to look for other jobs.
Stick with it.
– The first 1 on 1 is often kind of awkward, like a first date. You may have never had a candid conversation about their needs, frustrations, and desires before, which means there is often some guardedness. Stick with it, because over time, that awkwardness will fade. You’ll build a much stronger relationship with your team, which will have major impacts in the quality of all their work, their happiness on the job, and likelihood of staying with the company long term.
Want to have better one on ones? Need help staying on top of what matters most to your team?
Nobody sets out to be a bad manager and yet so many fall into traps and become one; it’s counter-intuitive to realize that humans are not straight forward machines. What worked as an individual contributor will not help you as a manager.
It’s easy to focus on the mechanical elements of management like company outcomes, hours logged, and project results, but that’s only a small part of what makes a great leader.
It’s so easy to stay professional instead of getting to know your team and what matters to them, especially if you’re remote or don’t interact with them every day. When this happens, is it any surprise they not only get frustrated or burn out but they don’t come to you with problems? Is it any surprise many bottle it up until they quit or find another job, which can lead to company-wide retention problems?
What do you do?Why do so many managers frustrate their teams?
The human element is missing.
If you help people achieve their goals, they’ll work hard for you to achieve the company’s goals as well. If you can align what you need them to do with what they want to do, the results can be great. If you make them feel important and recognize what they care about, they’ll work hard for you.
But all of this takes effort and time. Something that you don’t have unless you make time for it, which isn’t easy with all the emails, meetings and other responsibilities that come with a management role.
And rarely do such efforts get rewarded like specific company results do. So how do you make sure you’re not forgetting these things that pay off in the long term? And are you sure you are doing everything you could be?
I believe there is a way for today’s technology to help us all be better managers and caring leaders. If you’re interested in learning more, sign up below: