Team and leadership coaching
Your team is talking past each other and you don't know why
Meetings, activity, next steps — but nothing's really moving forward. People seem aligned, then drift. Work shows up that doesn't match what you thought was decided. You step in, clarify, things improve for a week — and then it happens again.
This isn't the kind of hard that leads somewhere. This wears people down, usually quietly. Your best people notice first. They stop pushing as hard, and some start looking around.
It's not that your team isn't trying. It's that clarity isn't sticking — and the longer that goes on, the more it costs you.
We help teams figure out what's actually breaking down — and work it out themselves so it stays fixed. No scripts. No performative alignment. Just the real work of getting a team to actually understand each other and move together.
Not sure yet? A 20-min session will give you a feel for how we work — no prep, no pitch — and a lot shorter than the real thing.
How we work with you
Every engagement starts with your actual situation. No templates, no default playbook.
Sometimes the issue is how leaders create clarity without slipping into micromanagement. Sometimes it's communication across functions, time zones, or seniority levels. Sometimes it's decision-making — who's involved, who feels heard, what actually sticks. Sometimes it's the rituals — what's helping, and what's quietly getting in the way.
We figure that out together first, then shape the work around it — so the change comes from inside your team, not imposed from the outside.
Individual coaching runs $2K/month, typically in 3-month cycles — three weeks on, one week off. Team engagements are scoped to the situation. We'll be direct about what makes sense — and just as direct if we're not the right fit.
Who this is for: Funded B2B teams where clarity isn't sticking and leadership knows it. Leaders tired of being the only ones holding the full picture.
Who this isn't for: Teams where leadership has already decided what the problem is. Individuals who want to be told they're right, not challenged.

What this looks like in practice
(This example is from a full-time role, not a client engagement — I was one of the people trying to make sense of the situation and move forward. It's one of many situations, formal and informal, where I've worked through exactly this kind of team challenge. That's the experience I bring to this work, team management or coaching.)
When I joined SoftServe as Design Director in 2021, I was part of a global team of 135 designers across Europe and the Americas. On paper, the challenge seemed normal, balancing pre-sales with operational functions: communication gaps, rough handoffs, and teams spread across too many time zones.
Then the war in Ukraine accelerated everything. The team had to expand into new regions almost overnight — Mexico, Colombia, Chile — adding more complexity, more pressure, and more distance between people.
Our team grew to 12 plus me and my manager, we were focused on product and service design. And the instinct to improve things was to use structure: better processes, clearer roles, tighter DesignOps. And that helped. But it didn't solve the real problem. The shift came from something simpler: creating space for people to actually know each other.
In our group, we moved status updates async. We used live time for something else — no agenda, no deliverables. The first few calls felt strange. Unproductive, even. Nobody quite knew what to do with the time and space. Slowly, people opened up. About isolation. About health. About what was going on in their home lives. One of my direct reports used the group as test subjects for a video game he was building on the side. We did a Zoom baking session — people cooking in their own kitchens, on camera, together. It sounds small. It wasn't.
We had a global Ops manager — a Ukrainian who held the institutional knowledge of the entire team in her head. She knew every designer's skillset, every project, every gap. When she eventually left, it took two people to replace her. But because we'd built the kind of team that actually talked to each other, we saw it coming. We had time to prepare instead of scrambling.
Trust changed. And once trust changed, everything else got easier.
Handoffs improved. Project friction dropped. The overall team grew to 200. The trust work didn't cause that — but it's what made the growth survivable.
— Skipper, SoftServe Jan 2021 to Jul 2024
This is a no pitch zone
Tell us where you're at
We'll talk through your situation and be straight about whether our approach makes sense for you and your team
Phone: +1 917-720-6388
Email: heythere@howthisworks.co
Book a call: howthisworks.co/start
Based in San Francisco, CA, working globally
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