How to navigate painful conclusions with your most trusted partners

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Hard news with the one I love most

I could feel my chest and shoulders tighten as my client described a recent conversation with her co-founder.

I don’t think she can run product for us anymore. It isn’t working. But I don’t know how to tell her. I’ve shared my concerns with her. But I don’t know how to find the words to tell her I’ve decided. That we need to replace her as head of product. She has been critical to our success so far, but it isn’t working anymore. We need someone who can take us from here to the next stage of growth. And I know it will break her heart.

There are moments in any partnership where it feels like there are no good options. Where the only choices on the table seem to be:

1) Betray myself and duck my own truth.

-or-

2) Hurt someone I care about.

Coaches often talk about finding a third option when only two show up. But sometimes there really are only two. And one of them breaks the heart of someone you love.

I’ve witnessed this many times recently from the coaching chair:

• A founding team where the co-founder leading revenue isn’t making progress.

• A first-time founder whose older co-founder keeps overriding her need for more support as the company grows.

• A client whose romantic partner wants to move home to be near family, while she feels tied to the Bay Area for work.

In each, the hardest part wasn’t the business decision. It was the threat of rupture to the partnership.

Humans can handle external threats. I’ve written separately about how our sense of danger diminishes when we’re near someone we love. But when our truth stands to hurt that very person, the opposite happens. The stakes feel higher. The nervous system tightens. The walls close in.

I’ve also written about how many founder-leaders grew up in families where we became responsible for the emotions of others. That’s not universal, but it shows up in so many of the leaders I meet. When this is your story, moments of hard truth can feel especially sharp.

In the session I mentioned above, I was brought back to one of the most painful moments of my own founder journey, which I wrote about here. I had to tell my co-founder, best friend, and VP of Product that he needed to step out of the role. It was not working even with the tremendous heart he put into it. We needed a change. I felt anxious and afraid. Afraid of losing my co-founder. Afraid of losing my friend. Afraid of getting it wrong.

In those moments, the best we can do is stay close to our own truth while holding compassion for the other person and for ourselves.

A few tools at hand

If you find yourself in a similar moment, now or later, here are a few tools I have found helpful.

1. Stay in your own truth

When fear says things like:

You are going to lose this person.

How can you hurt them like this?

You’re going to end up alone.

The work is to return to your own truth. If you are not fully clear, slow down and take time to find clarity. But if you are clear, stay in it.

It can feel kind to waver or soften your position, but as my old coach often reminded me, clarity is kind even when it hurts. It allows your partner to stand in the truth of your position. Wavering creates more harm.

2. Resource yourself

As you prepare to come with care and compassion, resource yourself:

• Journal
• Meditate
• Walk
• Work out
• Talk to trusted friends
• Speak with your coach or therapist.

Do not move through these moments alone. Especially moments where a key relationship feels under strain.

3. Come with compassion for the other

You can hold yourself while also holding compassion. Listen. Stay calm. Don’t rush an outcome. Don’t argue.

This isn’t a time to rely on intellect. Share your truth clearly and concisely. Then be with your partner. Sit. Listen. Be patient.

They may meet the news with shock, confusion, anger, or withdrawal. If they move into fight or flight, you may see the worst of them. They may be petty or harsh. Remember that they are hurting. This is not a moment to take things personally or expect their best self. Be with them where they are.

Take breaks if needed. Return later. Let compassion guide you.

4. Stay connected, even when it’s hard

If you step away, or if things get heated, keep small threads of connection alive. Remind them you care. Remind them you’re still here. Remind them that your truth does not diminish their worth or the importance of the relationship.

You’re not responsible for their emotional response or decisions. But you are responsible for keeping the connection where you can.

5. Let time play its role

Time always plays a role, especially when one person is in shock.

Humans are incredibly resilient. We can process heartbreak, loss, change, and grief. But often we need time to metabolize it.

Give time. Trust time.

6. Respect their truth and their decisions

When we share news like this, our own anxiety and fear often rise. We want the other person to receive it in a certain way. We want the relationship, company, or future to remain intact.

But the other person is an adult with their own agency. They get to respond as they choose. The more open-handed you can be, the more you reduce suffering for both of you.

7. Find new ground

As you both move through the hard moments, you will usually find your way to new ground. Maybe that means a new form of partnership, new roles, or a new phase of the relationship. It may take time.

Partnerships evolve. Businesses evolve. Families and friendships evolve. None of it stays stagnant.

Trust that as each of you shares your truth, stays connected, and moves through the difficult days, a new place will eventually emerge.

My co-founder and I have navigated many new grounds over the years. Best friends. Co-founders. Estranged partners. Distant acquaintances. And finally, back to close friends, allies, and collaborators. You can’t predict where your own story will lead. But the best way to honor any partnership is to tell the truth with an open heart.

It is not often easy.

8. Rinse and repeat as needed

You may move through these steps many times and in different orders. Trust your intuition. Trust your mind and your heart. Trust your compassion.

If I can support you in this journey, please reach out. You are not alone.

With love, from 10k feet in the air today.

Matt

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