Thoughtful, empathetic language can make or break your business relationships

Illustration: Leigh Wells/Getty Images

As a founder, my biggest regrets revolve around not having difficult conversations sooner. I could have helped team members improve faster, fired people with the wrong fit earlier, had so many more productive meetings. I could have created a more open company culture.

I was guilty of making excuses: It will sort itself out; they’ll eventually stop doing it; there are more important things to focus on. Of course, delaying these conversations always made things worse. …

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You need processes to scale… but how much process is enough?

New companies usually have few processes in place, so team members are often encouraged to ‘figure it out’. But as the team grows, so does the complexity.

The intuitive solution is to create standard processes and train your team to use them. However, as the number of processes grows, you may find your company becomes too rigid, slow-moving, and bureaucratic.

How do you strike the right balance?

Whenever you come across the word ‘balance’, try to clarify the two extreme ends. In this case, the extremes might be:

  • The ‘people’ extreme: People are free to choose how they complete their goals, even if their way doesn’t leverage…


The right choice is often ‘both’.

Life throws a lot of paradoxes at you. For example, you need to work as hard as humanly possible but you also need to have a life. You need to listen to customers but you also need to ignore them sometimes too. You need to be innovative and take risks but you need to stay lean and efficient as well.

While choosing one side of the paradox is delightfully clear and easy to communicate, it always leaves you with the downsides of the other. Yes, you’re working harder than your competitors, but at home you’re cruising towards a divorce.

How do you break the paradox?



Seven practices to help you stay energised and focused

There’s traditionally been a lot of focus on morning routines (what you do right after you wake up) and evening routines (what you do before bed) as ways to increase your performance

But my most powerful routines typically occur during the day. Here are some examples:

1) Lunchtime workouts

I work out Monday, Wednesday, and Friday, around lunchtime, and I have a large protein-rich meal for my lunch. I tend to do my best thinking after a workout.

2) Ad-hoc journaling

If I feel myself becoming overwhelmed or angry, I open my Remarkable journal and write for about 10 minutes. I start with the words, ‘I’m…


The opposite of a good idea is… also a good idea

When it comes to strategy, logic isn’t always your friend. Since most of your competitors have access to similar information, if they all followed the most logical argument, they’d all end up with products so similar customers would find it hard to differentiate between them.

Luckily, as Rory Sutherland points out in his book, Alchemy: The Surprising Power of Ideas That Don’t Make Sense, the opposite of a good idea is often another good idea.

Here are a few examples from his book, and a few others I’ve noted over the years.

What’s the right messaging for your product?

  • Not many people have this, so it must…


Great managers do this to set their team up for success.

In a previous essay on delegation, I suggested two principles that can help you delegate more effectively: (i) delegate problems, not tasks, and (ii) coach, don’t instruct.

What I missed was a third principal: (iii) empower problem-owners in public.

There are three steps to fully empower your team member and complete the delegation circle:

1) Signal the problem owner . . . to the team.

‘As you all know, we have a problem [problem statement]. I’ve asked [name of problem owner] to find a solution to this.’

2) Promote listening . . . to the team.

‘I’d like you all to help [name of problem owner] as needed. …


This simple format can help you get what you really want.

When you’re a founder, you sometimes have to ask people for something they may not want to give. Perhaps, you’re asking your investors to invest in a bridge round, or asking your team to work a particular weekend.

When you’re faced with the challenge of making a ‘hard ask’ without damaging the relationship, there’s a simple playbook:

1) Start with the most important facts.

‘We’ve just had the board meeting and got consensus for the new strategy.’

2) State the emotions those facts evoke in you.

‘I’m feeling excited but nervous, especially when it comes to fundraising.’

3) Link those emotions to your current needs.

‘Right now, I need to focus and spend time with the team, and I also need your support as…


Your board members can help you—if you ask.

How valuable do you find your board meetings? If you use them only to present results, share your learnings, or provide reassurance that you’re on top of things, you might be leaving value on the table.

Here are seven different ways of getting tangible value from board meetings, and how you might ask for it.

1) Opposing perspectives

‘I’d like to hear from someone who holds the opposite point of view. How did you come to this perspective?’

2) Experience

‘Has anyone been in a similar situation personally or via a portfolio company? What happened? What would you have done differently?’

3) Network

‘I need to meet…


Putting the gun in their hands can uncover their true colours

Photo by Anna Shvets on Pexels

Imagine you’re CEO of a small company. Your sales director has a variable bonus linked to new sales. During the year, the business strategy changes to deal with unforeseen circumstances. The sales director will now have to refocus on retaining existing customers, rather than acquiring new ones.

At year end, it’s time for their annual review. Under the original agreement, their bonus should be zero. You want to keep them motivated, but you also need to look after your business. It’s your call — so what should you do?

Putting the gun in your opponent’s hands

You might take inspiration from Bruce Dunlevie, GP of Benchmark Capital…


If your feedback cycles are too slow, try this.

The 360-degree feedback process can help employees and managers get a better sense of how they are perceived by others across their organisation. However, putting it into practice is time-consuming and mentally exhausting. Typically, it’s scheduled every 6–12 months — or avoided by startups completely.

The main issue isn’t with organising the process. It’s in the effort needed to write down nuanced feedback. Choosing the right words, and finding the appropriate tone is anxiety-inducing. In an ideal world, the conversations happen first and the written memo happens later.

And that’s why I love ‘speedback’ meetings (‘speed’ + ‘feedback’). They take…

Dave Bailey

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

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