Mature Start-up Running Out of Gas? Ask Madeleine

Dear Madeleine,

I am the COO and founder of what is now being called a “mature” startup. We have been around for 12 years but have not yet exceeded 100 employees or reached our revenue or valuation goals. The company still feels like a startup because we have been experimenting with our business model and the pace of innovation, and the constant pivots are relentless.

Some of our business leaders are tired of it. They are expressing attitudes that are not helpful, such as “If we were going to make it, we’d have made it by now,” or “What’s wrong with things the way they are? We seem to be doing fine.”

We are fine, but we have not achieved our full potential—nor are we as profitable as we need to be to attract investors. My original business partner, who is our CEO, has recently taken a leave of absence to deal with a family matter. He was exhausted. The last few years have been a slog and Covid was a massive setback for us. It seemed like the right time for him to take a break.

I am covering for him and struggling with the Eeyore-like outlook among some of my key people. I’ve been working on finding ways to inspire them. We put a lot more focus on self-care than any other startup I know. I’ve given feedback to some who are resistant to change and to what feels (to them) like risky ideas. It does not seem to be making a difference.

I still know in my heart that we are going to figure things out and break through, but I need everyone to be all in for this last push. How do I get my leaders on board?

Just About There

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Dear Just About There,

I’m a battle-worn veteran of a couple of startups myself—and now that I am nearing the last phase of my own career, your situation only confirms to me that startups are best suited for the young. I say this not to discriminate, but simply to point out that when the slog goes on for longer than anyone wants or expects, it can be hard to hold on to the giddy, cockeyed optimism required to stay in the game. The relentless pace of change can be exhausting, and you are going to need to find a way to tap into some of that initial startup energy you had at the beginning if you want to reach your goals.

I have a couple of ideas for you.

• Pay attention. Ask your people what specific concerns they have and listen in a way that makes them feel heard. I recently heard someone say “Clear communication is the oil that reduces the friction of living.” If your key people are turning into Eeyores (for the uninitiated, Eeyore is a character in the Winnie the Pooh stories who is depicted as having a bleak outlook on life), they probably need some attention. You may remember that Eeyore’s catch phrase is “Thanks for noticing me.” I wonder sometimes if leaders are afraid that listening and acknowledging people’s concerns means you have to do something about those concerns, when, in fact, simply listening often can make all the difference. You may think you are a good listener, and you probably are when you aren’t worn down by resistance. So if you want some technical tips on how to listen, you can find some here. For tips on managing constant innovation and change, you can access an excellent webinar here.
• Tap into personal motivations. It sounds like your leaders have run out of steam. There were specific things that drove them at the beginning, and anything you can do to help them get back in touch with those drivers will help. Maybe it was the promise of a big payout, or the ability to make an impact in the world, or the desire to be part of something cool and sexy. Whatever it was, help them remember it. Or maybe what matters to them has changed. If they are not going to be able to find it in their current role, it could be time for them to find another place that suits them better.
• Reclarify and rearticulate the vision. You and your partner had a big vision when you started. It is normal to assume that everyone has heard it and doesn’t need to hear it again, but that is incorrect. People need to be reminded of the big fat WHY all the time. It gets buried under the rough and tumble of the day-to-day slog. So dig for buried treasure, find the stories that will inspire, and tell them a lot more than you think you need to. This will undoubtedly bore you, because the vision is still so clear to you that you forget it is not as clear to others. Do it anyway.
• Stop giving feedback and start making clear requests. Feedback is tricky. We think if we do everything right when we give feedback, people will hear it, internalize it, and do something about it. That simply is not true. If you want your leaders to do things differently, you have to make a direct request. It needs to be crystal clear so that you don’t run the risk of it sounding like a suggestion. It is a request. For example: “Even if you disagree with the strategy, I need you to commit to supporting it and to make sure your team knows that you support it—even if you have your doubts.” You can point out specific dos and don’ts if you have examples. The kind of clarity you achieve with a direct request will help your leaders decide if they can commit or if they need to leave. This, of course, means some people may leave. But all you have is your people, and if your leaders aren’t with you, you need to replace them with leaders who are. This is harsh, I know. But it is true.
• Catch people doing things right. This is a classic bit of genius from Ken Blanchard and there is literally no situation in which it doesn’t apply. At the end of a long, grueling journey, it can be easy to pounce on every little thing that isn’t perfect. This can lead to an over-focus on pointing out what’s going wrong at the costly expense of directing focus on what is going right. You must make everyone feel that they are winning, even if it isn’t as fast or as evident as you would like.

It really does all rest on your shoulders, my friend. That is what leadership is. If it all goes sideways, everyone will blame you. And if you pull it off, you won’t get nearly the credit you deserve. If everyone could do it, everyone would be doing it, but it is the rare soul who has what it takes.

Put on your listening ears, share the inspiration, find and call out the best in people, and pray the gods will smile upon your efforts. Good luck to you.

Love, Madeleine

About Madeleine

Madeleine Homan Blanchard is a master certified coach, author, speaker, and cofounder of Blanchard Coaching Services. Madeleine’s Advice for the Well Intentioned Manager is a regular Saturday feature for a very select group: well intentioned managers. Leadership is hard—and the more you care, the harder it gets. Join us here each week for insight, resources, and conversation.

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