What it takes for CEO’s to scale up their companies

Dave Bailey is a London-based entrepreneur & investor who has co-founded and lead multiple companies in the UK and abroad. He’s mentored leaders at companies such as Google Launchpad and Techstars. He was a tech columnist for Inc. Magazine and currently writes for his own blog, The Founder Coach. Read his full bio on Dave’s website.

After 10 years in the Venture Capital industry, Dave started coaching CEO’s of Series A and B companies on scaling their businesses. The need for CEO-coaching was clear, but the business was “non-obvious” (especially in the UK at the time) — leaders were sceptical! CEO-coaching became very popular in the US and later took off for Dave in the UK as well.

What really inspired us, is this article that Dave wrote on why every CEO needs to hire a Chief of Staff.

“One of the biggest demands of Founder time, especially in the scale-up phase, is recruiting.”

This is one example where the Chief of Staff resource could help with the more administrative coordination of the company, so that the CEO could spend their time more wisely in interviews & actually meeting and hiring the right people.

Some of the biases Dave has seen in young companies:

  • Misunderstood Marketing. People tend to be confused about what role marketing plays in the company.
  • The perception that HR is the part of the company where people go to complain.
“HR should be the coaching department… not the moaning department.”

One of the most useful terms that Dave has learnt in his coaching, is “colluding”. When someone complains to you, you adopt the negative mindset of the other party. It’s not helpful. This is where coaching can help people take responsibility & regain control of situations again — by recognising negative mindsets and adjusting or accepting situations in order to resolve and/or move on.

This process will help HR become what it’s meant to be: the place where people can go to give their hard feedback to the company.

“There’s a fascinating relationship between process and empowerment.”

Process is what happens when the individual is not trusted and you want to enforce the right behaviours. On the other hand, with too little process it will not be understood what is expected of the team.

How can management take responsibility for culture?

Culture should be something you hire and fire for. Culture can be built by incentivising certain behaviours that will contribute to your success. Culture is also that which attracts new hires. If you’re not intentional about the culture, it will form nonetheless (whether good or bad) — but the leaders always set the tone.

“One of the roles of leadership is to figure out their own dysfunctions and work on themselves, because that’s one way to impact everyone else.”

Leaders tend to be very assertive, even when they think they’re not assertive enough! This comes with a lot of personal issues that need to be dealt with. Oftentimes these assertive CEO’s believe their company culture is very open, but in reality there is a very clear power divide. To break down this divide, you need to spend time with your staff and build up trust.

“The first hour of a meeting is usually superficial. The second hour is when the juicy stuff comes out!”

Enjoy! Hit play ▶️ above to watch the interview video.
Search and add us on your favourite podcast app: Anchor // iTunes // Pocket Casts // Overcast // RSS and more…


Timestamp notes:

0.23 — Dave introduces himself.

1.00 — How Dave got into the Coaching business.

2.59 — What is Dave’s №1 regret?

3.12 — Dave’s coaching process.

3.39 — When is a good time to get a coach?

5.00 — Why every startup needs a Chief of Staff.

10.55 — The bias against HR.

14.23 — What to look out for when hiring a Chief of Staff.

18.10 — Dave’s view on company culture. What stops companies from innovating?

23.25 — How to increase self-knowledge.

30.50 — An average day for Dave.

31.56 — What is Dave reading? From Impossible to Inevitable (Ross & Lemkin), The Success Formula (Andrew Kakabadse), books about mental models. His best recent read is Attached: The Science of Adult Attachment (Levine & Heller).

35.00 — Software he uses daily? Productivity tool: Rev.com (audio transcription). Automation tool: Zapier to automate manual tasks. Recording tool: Loom as a low-friction, asynchronous alternative to text, and great for a remote team.

40.18 — How to reach Dave: Medium, Twitter, LinkedIn, Website

If you have any feedback, comments, ideas or suggestions, please get in contact with us on twitter @giveahi5 or email us on podcasts@get5.io.

Need help scaling up your HR? Try Hi5 (14-day free trial).

Get the podcast

Don't miss these episodes

Non-political, values-driven work

Nadia Vatalidis, People Operations Manager at Gitlab, chats to us about their all-remote, values-driven company culture & how they scaled to 767 employees.
Check it out

How design-thinking helps HR.

In this episode of Working better, together, we chat to Melissa Hui from Context Leap on people + culture design.
Check it out

The 5 Languages of Appreciation in the Workplace

We chat to Dr Paul White, experienced psychologist & speaker, and co-author of book The 5 Languages of Appreciation in the Workplace.
Check it out