Capability 11 · Lead Others
Know & Use the Right Leadership Hat
A first-time founder ran every 1:1 in advice mode until the hats reframe — now his smartest engineer arrives with options and leaves with her own plan.
Founders say
“I hired smart people, but somehow every conversation ends with me telling them what to do. I'm exhausted — and honestly, they've stopped thinking.”
Where you are today
- Every 1:1 turns into you dispensing solutions — it's faster in the moment, so it keeps happening.
- Your best people wait for instructions, because instructions always come.
- You use the same voice for a production fire and a career conversation.
Where you’re headed
- You catch the moment mid-conversation: this needs the coaching hat, not the answer.
- Smart people leave your 1:1s with their own plan, not your to-do list.
- The formal calls — the no, the review, the salary conversation — get made cleanly instead of avoided.
Why this matters
Managing people is an honour. The most meaningful part of my own startup journey wasn't the product or the fundraise — it was the lives changed by being a good boss and building a good environment. Whatever happens to your startup, giving good people real opportunities and space to grow changes lives. And the day-to-day leverage point is smaller than it sounds: knowing which of four hats — coach, mentor, empower, manager — this person, in this moment, actually needs.
What this means
- Switch deliberately between coach, mentor, empowerer and manager, depending on the person and the situation.
- Default to coaching where you can: help people think for themselves and leave them more capable after each conversation, rather than handing over answers.
- Notice your own default hat and where it creates bias, and choose the mode that best serves the person's growth and the outcome.
What good looks like
- You can name the four hats and know, per person and per situation, which one you're wearing.
- The coaching hat gets real use: "What do you think?" asked with genuine curiosity — leading them to their own answer, not quizzing them toward yours.
- You still wear the manager hat when it's called for — saying no, running the review, negotiating the salary — without dressing it up as something softer.
Where founders get it wrong
- Always telling people the next step. They don't grow, you don't scale — you've made yourself the ceiling.
- Coaching while the building is on fire. The production server is down and you're asking "how do you feel about this?" — wrong hat.
- Treating the formal side — vacation approvals, performance reviews, salary talks — as an interruption to leadership instead of part of it.
There's no right or wrong management style — direct and collaborative both work. A lot of it is gut feeling. The skill isn't picking a style; it's the reflection: "Which manager hat am I wearing right now?"
The hats get their reps in your 1:1s — that's where you'll catch yourself defaulting to one mode. And the coaching hat comes with a cheat sheet: seven questions that lead people to their own answer instead of yours.
What you can do right now
- Audit your last three 1:1s. For each: which hat were you wearing, and which did the moment actually need? Most founders discover one default hat worn everywhere. Leadership Hats →
- Ask "What do you think?" first. With your smartest report this week, hold the advice back. Three curious questions before you offer anything.
- Name the hat out loud. "I'm putting my manager hat on for a second" tells people what kind of conversation this is — and makes the switch visible to you too.
The toolkit
Work with Ben
Want help installing this?
Outstride OS is the system behind Ben's founder coaching — pre-seed to Series C. If this page names something you are living right now, start a conversation.