The most important word for motivating your team

Progress. It’s a word that has driven man for generations to grow, develop, learn, and reach for the stars (sometimes even literally). It often feels stale and disheartening when progress isn’t being made.  There’s a reason that Elon Musk, Jeff Bezos, and Richard Branson have all invested in space travel; NASA stopped making progress and they were all inspired to push to advance mankind to space.

For us mere mortals, progress may not be measured on a societal scale, but we all still have goals. These goals are what drive us and motivate us to get up in the morning. As a manager, you are not only accountable to your own goals, but that of everyone on your team.

Do each of your team members make regular progress on their goals? Do projects drag on for months, or do they see results of the fruit of their labors on a regular basis? Whether you’re in sales, marketing, engineering, design or support, progress is hugely important to the mental well being of every team member.

The stakes for progress on your team couldn’t be higher. Engineers that don’t ship product for months have a high propensity for burn out.  Employees in any department will become frustrated and seek challenges at new companies if they feel like they’re no longer growing, learning, and working on things they’re excited about.

As a manager, you need to help your team make progress: Ship. Close deals. Get wins. See results.

But how do you reliably do this? How do you get out in front of potential disaster?

How to ensure your team members are making regular progress

1) Remove Blockers

Few things are as frustrating as feeling like you can’t get your work done because of someone else. Waiting for decisions or dealing with someone who is a bottleneck in a work flow can quickly stall out even the most talented person’s ability to make progress.

As a manager, you can often be the cause of those blockers. Diffuse that source of frustration for your team as much as you can. A great lesson I learned from Jonathan Kay, CEO of Apptopia, is to regularly ask everyone on your team, “Am I blocking you?” and then follow through on anything they ask for you to help them with right away.

When you meet with your team, always ask them if they’re being blocked in any way. The more you can help remove the blockers (even when you’re not directly responsible), the more your team will be able to get done and feel productive.

2) Empower Your Team

Are you a dictator that rules with an iron fist, making every little decision for your team? Or do you delegate effectively to your team, trusting them to make decisions on their own in their areas of expertise?

As a manager, there are too many decisions to make to micromanage everyone. You become much more scalable (and less likely to block them), when you let your team make the little decisions in their jobs. You also are then empowering them to have ownership over their work and focused on accountability to you on the results.

Work with your team to set the goals and expectations, but trust them to do the work you hired them in the best way they see fit. If you can’t trust them to do so, you need to hire people you can trust.

3) Align goals

Every person has different motivations and interests. If you understand what their goals are, you can help them get on the right projects with the right responsibilities. When someone’s work is aligned with their personal and professional goals, you will see them operate at their highest possible performance level.

As a manager, you need to regularly talk about each team member’s goals and interests. Not only will they differ person to person, but they will also change over time. Yee Lee, VP of Engineering at TaskRabbit, reminds himself to check with every member of the engineering team at least every 3 months to see if their long term goals have changed (they often do for many reasons). This ensures that everyone is making progress on their goals and the company keeps everyone aligned with what their asked to do on the job.

4) Watch for warning signs

Every big problem started out as a small one. The more you can identify problems when they’re small, the more likely you are to avoid having to constantly triage major issues that will take up all the time you don’t have.

When projects are making less progress or dragging on, you can often tell based on a shift in morale. Look for signs that people are not as engaged in a project or seem to be growing in frustration. What seems small to you on the outside may be a big issue brewing for those on the inside on a project.

The best early warning is your one on ones. When you ask them how something is going one on one, they’re more likely to be candid than in a group and you can also dig a little deeper by asking revealing questions such as, “What’s the most frustrating part of our project you’re working on now?” Whatever you hear, act on it appropriately and you will not only diffuse the situation, but build trust in your team that they can bring important issues to you no matter the size.

5) Take no one for granted

It’s easy to think that someone who crushes it at their job will want to keep doing it forever. Unfortunately, times and motivations change for everyone and, if you’re not careful, you will lose people when those motivations shift.

You need a strong communication channel to keep your best people. If they trust you, they will tell you.  Joe Stump, co-founder of Sprintly, had a great engineer who told Joe that he wanted to try something new (in his case, marketing). As much as Joe hated losing an engineer, he hated losing a talented team member even more, so Joe worked with the engineer to shift to a growth hacking role they were excited to do and the company needed.

As a manager, it’s easy to spend all your time on weaker team members or people that need the most mentorship. Don’t forget to check in on even your best talents or you may find out when it’s too late. This is why you should do one on ones with *everyone* on your team.

Your people are motivated by one word: Progress.  Are you helping them get there?


Get LighthouseGreat managers help their team make progress on their work, their career goals, and fix problems while they’re small.

If you’re looking for help making *progress* on these things, then give Lighthouse a try. It keeps you organized and helps you follow the best practices of great leaders. Learn more at GetLighthouse.com

Does Boston Have Too Many Startups? A response to Kirsner’s Sunday Globe Article

This post originally appeared on Greenhorn Connect and has a boatload of comments. See here: https://greenhornconnect.com/blog/does-boston-have-too-many-startups-response-kirsner-s-sunday-globe-article

In the Sunday Globe this week, Scott Kirsner posed the question, “Does Boston Have Too Many Startups?”  The article seemed to try to make the argument that all our little startups should just be employees at bigger startups (disregarding how bigger startups, start out…).

The article is really best summed up in the quote in the article by Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.” I find it fitting that coincidentally, Ryan Durkin, COO of CampusLive (and mentee of Mr. Driscoll as a Highland Capital portfolio company) writes about attracting talent today:  http://www.ryandurkin.com/blog/2011/10/how-to-hire-dudes-showers-kitchens/

I’ve spoken with a number of friends about the article and had some interesting Twitter conversations as well and wanted to highlight some of the key points that came from them.  (Note: Kirsner sought out some thoughts which you can see on his Globe blog here.)

1) We don’t talk about logical career paths enough

Quick: explain, with examples, a logical career path for someone to evolve to be a successful entrepreneur.  Stumped? I know I am. Most examples I think of fit in the “Zuckerberg” files of folks who didn’t have much of a startup pedigree before launching their monster success (think Matt Lauzon, the many TechStars companies, etc).  I look at the titans of our community like David Cancel, Dharmesh Shah, Jeff Bussgang and know very little about “how they got here.”

It’s easy to tell people “go work for a startup first,” but you need to show them examples of people that have succeeded in doing that, and if you didn’t as a founder, then you have to acknowledge you have some hypocrisy on your hands.

2) We don’t have enough serial entrepreneurs and mafias

We are all familiar with the Paypal Mafia and some of the many startups the former employees spawned, but where are Boston’s Mafia’s? There was a great Bostinnovation series covering some of them, but it seems like there are fewer and certainly less celebrated.

These mafias are exactly what would convince someone to *join* a startup instead of start their own: join a team and have a great exit and then have peers and valuable experience to start another.  Maybe an offshoot of Eric Paley‘s Founder Dialogues needs to be “Mafia Dialogues” and bring in a few people from a successful team to share their combined story. We also need to think about whether it’s good for a CEO of a billion dollar company to be proud that all of his first 10 employees are still working at his now billion dollar company.

I think Rob Go was also on the right track highlighting the power team of Brian Balfour, Aaron White and Ariel Diaz teaming up for Boundless Learning (and also happens to talk about the importance of “more shots on goal,” not less startups as Kirsner suggests).

3) We don’t take enough chances on Greenhorns

I am very lucky. What few of you remember is that no one was interested in hiring me when I came into the tech scene. John Prendergast was the first to give me a small shot doing some work for him, which then led to the opportunity to pitch Laura and the oneforty team on joining them (John was on their board).  That was a 6 month journey to get that full time offer from oneforty.  If I didn’t live as lean as possible and have the luxury of a little savings, I may have never made it.

Just like our investors are often criticized for wanting too much traction before they invest, many of our companies only want to hire people that have done a role before.  I know too many young, eager people who want to work at startups, and yet there doesn’t seem to be many roles available to them.  I get asked about Janet Aronica, who I hired at oneforty, a few times a month it seems and the irony is, I doubt anyone else would have taken a chance on a young, eager talent coming from the low rungs of a PR firm.  I also look at Kristin Dziadul, who once made videos trying to get HubSpot’s attention and was smartly hired by Rob May and Backupify.

This is not to lump everyone together. Matt Lauzon and the Gemvara folks have taken chances, and I know Diane Hessan has been an awesome advocate for some of the truly hungry Gen Y folks. Unfortunately, the rest of the community hasn’t caught on yet.

4) We don’t take recruiting seriously

It bears repeating via Craig Driscoll, “companies that hope to grow need to do more than complain about how tight the talent market is.”  Vinod Khosla went as far as to say “New CEOs should spend 50% of their time recruiting.”  I’ve seen the aggressiveness of Sequoia firsthand as they held an event the night before Startup Bootcamp for their founders who were speaking to tell a bit of their stories, answer questions and meet people. I know Dropbox has spoken at at least 3 Boston area schools in the last 6 months.  How many schools have you spoken at in your own back yard?

Maybe we need an event or two to talk more about recruiting talent (One of my favorite events ever was a fireside chat with Akhil of MassChallenge and Paul English talking about recruiting).  I think it’s a competitive advantage for some companies while others throw money at it, but it certainly seems like it might help.  More awesome posts on the subject like Brian Balfour’s and David Cancel’s would help too.

5) Complaining about funded startups is an insult to entrepreneurs

The funding climate in Boston has improved, but it’s still hard to raise money.  As the opening to the Bloomberg TV show states, TechStars is more selective than Harvard. If you manage to raise money, that’s quite an accomplishment, as David Friend says in his message to Kirsner.  If you have an idea that goes far enough to funding, you have an at bat and need to go try to execute. The amount you’ll learn with your small team will be tremendous and put you in a great position to contribute to another company.

Now, living off of savings, is obviously a big risk and so if someone is risking financial ruin to keep their fledgling startup alive, it most likely makes sense to go work somewhere. Then again, the Valley wouldn’t have Airbnb if those guys weren’t relentless.

6) We need to clarify what a startup is

Wayfair is a $350Mn+ company. HubSpot has over 300 employees.  Are both of them still startups? Neither? I worked at E Ink when they went from about 90 employees to 165.  From my experience, the Dunbar number is very real.  The culture really started to shift at that point and more HR rules and regulations hit, not by choice, but out of necessity.  Few companies are really like Google and provide the independence and opportunities similar to startups, and even there, I don’t think you get the same thing.

I’ve heard about HubSpot’s education classes that try to teach some business and entrepreneurial lessons, but I have a feeling they’re the exception, not the rule. I also wonder how they’ll be able to maintain it as they grow further.

7) What motivates an entrepreneur or early stage employee?

Another great quote from Craig Driscoll on advising companies was, “They need to figure out how to recruit and create jobs that are attractive for entrepreneurial people.”  An entrepreneurial person cares much more about working with other smart people, having flexibility and independence in their role and a feeling of true contribution and influence in the big picture of what they do.

When I worked at E Ink, everyone looked forward to their quarterly meetings where Russ Wilcox explained the state of the company.  It lifted the covers on how the company was doing and especially during the wild ride that was the exploding popularity of the Kindle, you could feel everyone having a renewed sense of purpose after work as they were a part of the amazing opportunity to replace paper books with E Ink technology.  I think that same sentiment is happening now with Gemvara as Matt hammers home the vision to change jewelry and e commerce on the web.  Entrepreneurial employees want to be a part of something bigger than themselves, while feeling like they’re really making a contribution.

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I’m glad Scott brought this conversation out for discussion, but feel like it missed the mark on what really matters in this ecosystem developing.