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‘That’s irrational.’

‘That’s stupid.’

‘They’re making things difficult for the sake of it.’

When we encounter emotions and behaviours that don’t make sense to us, it’s often because we don’t have all the information. And in the absence of information, we tend to assume the worst.

‘Emotional generosity’ is the ability to see past behaviours that we don’t understand and proactively look for compassionate ways to explain them. It’s easy to do this for young children. If they start crying or throwing a tantrum, we wonder whether they are hungry, or tired, or hurt. Sadly, it’s harder to do this…


Selling the dream is a key part of a founder’s job — whether that means convincing investors to invest, prospects to buy, or candidates to join the company. Of course, existing relationships can be a big asset. However, when you’re starting, outbound prospecting is an important way to expand your network and build new relationships.

The most common approach to prospecting is an intuitive one: you reach out, see what happens, and then try again. Quickly, you learn it’s a numbers game. …


What makes leadership team meetings trickier than they should be?

That’s a question I’ve been asking a lot of CEOs, both on my podcast and my coaching programs. Frequent answers include:

  • A lack of alignment over the objective of the meeting
  • A lack of clarity over people’s roles
  • A lack of trust between members

However, even if these aren’t issues for you, some team meetings can still be difficult — and that’s down to how our brains work.

Creative problem solving requires two very different cognitive processes: divergent and convergent thinking:

  • Divergent thinking is the process of coming up with…


Most leadership teams come together for at least a few days each year to meet up as a team, align on the business strategy, and collaborate on the company’s biggest challenges. These meetings are often held offsite, as physical distance from day-to-day operations can make it easier to see the bigger picture.

The pressure to deliver something tangible can make setting the agenda an intimidating task. There are many topics you could discuss and alignment can seem a long way away. How can you make the best use of your team’s problem-solving abilities and arrive at something concrete?

I’ve created…


Being held to account for our decisions, actions, and results can drive high performance. It helps clarifies our commitments, increases our diligence, and improves our self-awareness.

Most of us report to someone. For CEOs, it’s a board of directors. For others, it’s their manager or their coach. But despite all our reporting structures, real accountability is elusive for many teams.

Why Accountability Slips

The main reason accountability isn’t held is because holding people to account feels confrontational for both the report and the manager.

For the report, answering a barrage of questions can feel like an inquisition. Top performers often spend time predicting…


One of the hardest parts of the journey from founder to CEO is to let go of the details. It’s as painful as slowly pulling hot wax off their legs (or so I assume — I haven’t waxed my legs recently).

However, there is a simple way for CEOs to speed up the process, and metaphorically rip themselves from daily operations with minimal pain.

Take a two-week vacation.

‘Absolutely impossible,’ I hear them say. ‘The company will fall apart!’ And, of course, what happens next is quite predictable.

The CEOs begin to burn out and eventually have to accept that…


Here’s the scenario. You’re coaching a colleague in a one-on-one meeting and they commit to an action you both agree needs to happen. Although this is the last step in the ‘GROW’ model of coaching, you have a niggling feeling that they’re not going to follow through.

What can you do to increase the chances they follow through?

Many people instinctively reach for incentives, i.e., carrots and sticks. However, as I’ve written before, extrinsic motivators can backfire. But there’s an underestimated technique that can increase rates of follow-through, and that is to ask visualisation questions.

A visualisation question is one that forces someone to simulate doing the task in their mind…


There are basically four ways to take a decision:

  • By command — a decision is made by an individual without consultation
  • By consultation — a decision is made by an individual after consulting other group members
  • By consensus — a group decision is made once everyone agrees
  • By counting votes — a group decision is made by majority (like a democracy)

Group decisions may sound like a good idea, but what often emerges are compromises, with no passionate owner. ‘Decision by consensus’ is slow, and ‘Decision by counting votes’ quickly becomes political.

On the other hand, empowering individuals also sounds…


Lockdown has taught me many things, but there’s one lesson that can’t be overstated. Don’t give nuanced feedback via Slack. Or via SMS. Or WhatsApp.

Messaging is awesome for lots of things, but nuanced feedback isn’t one of them. The problem is you have absolutely no idea what’s happening on the other end of the chat — and the recipient’s emotional state has a huge impact on how they interpret the message.

For example, if they are already stressed, angry, anxious, or irritated — say, by the crying baby in the next room or because they missed breakfast — they…


OKRs (objectives and key results) have become so popular that they’re quickly becoming interchangeable with their sister acronym, KPIs (key performance indicators).

I know you aren’t confusing these terms, but just in case you have a colleague who is, here’s a useful distinction.

1) OKRs are for new initiatives

When you’re building something new, you want an inspiring and ambitious objective along with a clear measurement of success. When it comes to objectives and key results, aim for as small a set as possible to increase focus. …

Dave Bailey

CEO coach to Series A+ founders, 3X venture-backed founder, angel investor, author of The Founder Coach ->

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