Not Sure You Want to Stay with Your Company? Ask Madeleine

Dear Madeleine,

I manage a small team for a startup health and wellbeing subscription platform. I was super excited at the beginning—the founders seemed to have the right values and care about their employees. As time has passed, though, the competition has increased and none of the strategic targets have been met. With every all-company meeting, the strategy changes and we all feel like pinballs.

Many of our competitors are laying people off in droves. In the meantime, our company has brought in a lot of investors and heavy hitters from our competitors who bring their favorites with them, so there is a very weird dynamic of factions in the company now. We’ve got the old-timers, the Team X people, the Team Y people, etc. All the new groups seem to think they are special and are downright rude to the original folks. At a recent in-person team building retreat, no effort was made to integrate the old with the new. It was poorly planned and a colossal waste of time and money.

My original boss, who I loved and who was a great manager, recently left. It was not made clear why. My new boss came from a competitor. She can’t remember my name and is making it obvious that she wants to replace me with one of her pets. She keeps cancelling our one-on-ones but my team keeps hitting its numbers, so she can’t really fault me. Still, I can’t help feeling like my days are numbered.

None of the promises the company made at the beginning have been kept. A lot of the attraction at the beginning was having equity in the company, but now that it feels like the ship is going down, I can’t see that it will be worth much.

I am torn between the loyalty I felt at the beginning and the disillusionment with leadership I feel now. I would hate to walk away from the equity I was promised, but I just don’t know how much longer I can hang on.



Dear Torn,

Startups are notoriously messy and many fail. There are a lot of reasons for this, outlined nicely in this article. The competition in your space is particularly fierce as companies try to attract members and retain them. The overwhelming tone of your letter is disappointment. Disappointment is one of the most unpleasant emotions and can be very hard to face head on. But burying it by putting your head in the sand won’t save you.

I have a few thoughts for you, and you aren’t going to like any of them.

I think you need to honor your own intuition that the top leadership has lost its way. Where are the values that were discussed at the beginning? Are they in writing somewhere? Are they being used to onboard the new people? Are they being used to manage leadership performance? If not, they are an idea that was never executed and might as well never have existed.

I can’t tell if you have actual equity (a.k.a. a written contract) or if it was a verbal promise. If you don’t have anything in writing, I hate to say it, but you’ve got nothing. And even if it were in writing, if you really think the ship is going down, part of nothing is nothing.

Now this new manager situation. If it is okay with you to work for a manager who doesn’t seem to care one iota about you, it is your choice. But, again, you have a very strong intuition that it is only a matter of time before you are ousted. So unless you have a history of being suspicious of dubious behavior and being proved wrong, you are probably right.

I am a big fan of loyalty but it sounds like the vision that captured your heart is gone and the people that built that loyalty have already left. So what and who exactly are you loyal to now? I also love optimism. As someone who has led several startups myself, I can tell you that optimism is critical until it blocks out reality, at which point it becomes toxic.

It really sounds like you know what you need to do but don’t want to admit it to yourself. No one would blame you for feeling torn—you have all of those initial relationships and you worked hard through the first couple of startup phases. No one wants to walk away from what felt like an investment.

Ask yourself “If one of my best friends outlined this situation and asked for my advice, what would I say?” And there, my disappointed friend, will be your answer.

There is a lot of opportunity out there. I highly recommend you go find some leaders worthy of your loyalty, your work ethic, and your hard-won experience.

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.

Got a question for Madeleine? Email Madeleine and look for your response soon. Please be advised that although she will do her best, Madeleine cannot respond to each letter personally. Letters will be edited for clarity and length.

2 thoughts on “Not Sure You Want to Stay with Your Company? Ask Madeleine

  1. Hi Madeleine, your advice on loyalty was good. We all know those employees who are loyal to employers who don’t deserve it and it’s sad to watch. Turning the question around on what advice they would give a friend will help them find the right perspective.

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