Tackle Self-Doubt and Build a High-Performing Leadership Team

You’re scaling fast - funding’s in, headcount’s growing, and expectations are higher than ever... But under the surface you’ve got a leadership team doubting themselves, holding back in meetings, second-guessing decisions. And if you’re honest, you’re sometimes doing the same.

This isn’t just about you as a founder. It's systemic. And if you don’t address it, it becomes cultural.

Imposter Syndrome Isn’t the Problem - It’s the Signal

You and your team might be feeling like frauds. But that feeling? It’s rarely about competence. More often, it's about:

• Lack of clarity on expectations

• No feedback loops

• Workloads that are unmanageable

• A culture where performance = survival, not growth
  

What to do: Audit your environment before you start dissecting confidence.

Ask:

• Do my team know what great looks like?

• Are we regularly reviewing success and failure in a constructive way?

• Is there space to ask “Am I doing this right?” without fear?
  

If not, you're not failing - you’re under-investing in leadership infrastructure.

How to Build a Feedback Culture That Drives Performance

Let’s bin the annual appraisal fantasy. In startup reality, your team needs fast, meaningful feedback loops - not retrospective reviews or awkward “sandwich” chats.

Most startup leaders avoid giving real feedback because they either don’t want to upset people, or they swing the other way and come off like a blunt instrument.

Enter: Radical Candour.

Coined by Kim Scott (ex-Google, ex-Apple), Radical Candour means challenging directly while showing you care personally. It’s the sweet spot between being a pushover and being a jerk. When done right, it creates trust, accountability, and growth.

If you're too nice and avoid challenge? You get stagnation. Too direct with no warmth? People stop listening. But get it right, and you build leaders who grow, own their performance, and raise the bar.

Use the ACORN model to structure feedback:

• Acknowledge – Recognise the person and their value to the business. “You’ve been a key player in keeping the release cycle on track — I know how much you’re juggling at the moment.”

• Context – What are you referring to? “I wanted to talk about how the last-minute API change was handled ahead of the client demo.”

• Observation – Describe the facts without judgment or assumption. “The change wasn’t flagged to the product team until after it went live, and the documentation wasn’t updated.”

• Result – Spell out the impact, so they understand the wider consequences. “That created confusion during the client walkthrough and undermined confidence in the stability of the platform.”

• Next steps – Focus on what needs to happen moving forward. Offer support if needed. “Let’s put a simple sign-off process in place for late-stage changes. I’m happy to help define it - we just need to tighten things up without slowing delivery.”
  

Feedback should be frequent and fast. The best conversations happen in two minutes between meetings, not saved up for performance reviews. Done right, feedback isn’t confrontation, it’s calibration.

High Performers Are the Ones Most Likely to Doubt Themselves

Here’s the paradox: your most driven, high-performing leaders often feel like they’re not doing enough. Why?

Because they set impossibly high bars. They minimise their own impact. And they assume everyone else has it together.

Your job as founder? Recalibrate reality.

• Show them what “good enough” looks like. Perfection isn't always needed.

• Celebrate value delivered, not just effort spent.

• Help them see the compound effect of their work - not just what’s left undone.
  

You’re not just building a team. You’re building internal narratives. Make sure they’re not silently spiralling.

Authentic Leadership: Lead with Integrity, Not Imitation

In the chaos of scale, it’s easy to think leadership means having all the answers, all the time. But your team doesn’t need a robot in a Patagonia vest - they need a real person they can trust.

Authenticity isn’t about oversharing or being “nice.” It’s about leading in a way that’s consistent with your values, even under pressure.

Research shows authentic leaders are self-aware, say what they mean, and act with integrity - even when it’s uncomfortable.

You don’t need to be perfect. You need to be predictable in your values, your decisions, and how you show up.

That means:

• Be transparent about tough calls (especially when they impact others).

• Own your mistakes. People respect humility more than false certainty.

• Don’t try to “perform leadership” - model it through consistent behaviour.

Authenticity isn’t fixed - it’s iterative. Think of it like product-market fit, but for your leadership style. You prototype, you test, you adapt and it gets stronger over time.

Redesign the Environment Before You Rewire the People

If you’re seeing recurring leadership anxiety, chronic second-guessing, or silence in senior meetings then it's time to take a look at the environment, not just the individuals.

Ask:

• Are we onboarding leaders, or just dropping them into the fire?

• Do people know the outcomes they’re responsible for, not just tasks?

• Is our calendar a reflection of what matters… or just noise?
  

How to Fix the Environment:

• Structure mentoring, not just management.

• Create psychological safety to fail fast and fix faster.

• Be crystal clear on what success looks like - then repeat it often.
  

This isn’t about being soft. It’s about building a performance culture that doesn’t collapse under pressure.

Self-Doubt Is a Leadership Issue — and a Cultural Opportunity

If you want a team that scales with you, not against you, you need to normalise uncertainty without lowering standards. That means:

• Clear expectations

• Consistent, empathetic feedback

• An authentic leadership style that’s confident without being performative

You don’t need to fix everyone. You need to build the conditions where your team can grow, speak up, and get out of their own way.

And that starts with you.