How leaders can let go and grow

If you are the founder of a scaling, mid-sized company, do you ever feel the weight on your shoulders?

You need to find the winning strategy that will let your business accelerate. Once you’ve figured out what that might be, you also need to delegate more tasks, because there is only so much you can do on your own.

You don’t want the business to suffer if you let go too much. But what if you have become the bottleneck to growth?

These are common headaches, says Caroline Webb. She is a British business coach based in New York, an ex-economist at the Bank of England and a senior advisor to McKinsey, where she helped to set up its leadership programme.

You may also recognise her as the author of the bestselling business book How To Have A Good Day. Her latest book is called Leadership Intelligence. I spoke to her about it on one of her visits to London.

In my interview with her, you will learn:

• How to brainstorm strategy for your business in a practical way
• How to delegate so you empower colleagues and lighten your mental load
• How to graduate beyond ‘founder mode’

How to find a breakthrough strategy

Scaling, mid-sized businesses typically don’t have the luxury of a research department, or perhaps the capacity to bring in consultants. So founders have to initiate a lot of brainstorming themselves. The challenge often involves having to understand a complex situation with plenty of ‘unknown unknowns’.

To do this, they need to go into what Webb calls “exploratory mode”, which will help them “widen their field of vision”, so it’s closer to 360 degrees.

“It starts with understanding that you're not seeing the full picture,” says Webb. “This is just how our brains work. Our brain does a wonderful job of making it feel like we're seeing and hearing everything, but we're actually not. We're seeing a very tiny portion. So, you want to develop this habit of saying, ‘Okay, I understand this is what I think, but let me set it aside; let me assume I'm wrong in some way and let me get curious’.”

This means a different way of interacting with your team.

“It requires a coaching language and a lot of entrepreneurs are more used to being quite forceful,” says Webb.

So, instead of using confrontational questions like ‘Well, this is a problem, isn't it?’, you might say, ‘How do you see this? What's your hunch about what's going on? Tell me what makes you say that.’

In these types of group meeting it’s important that the leader signals that they are curious, open and willing to learn. People naturally fear upsetting the boss, but this must be an open conversation focused on evaluation and not recrimination. Indeed you must reward openness, says Webb, even when it’s about negative news and “never shoot the messenger”.

Try ‘brainwriting’ in groups

It’s also important to ensure everyone in the team has a chance to input their ideas. Some people might be more introverted and dislike these situations.

Silent brainstorming before a meeting, also known as ‘brainwriting’, where you write down your thoughts on a topic before sharing your ideas in a group, is one way to address this.

Webb’s other tips include:

• Go and see for yourself what the problems are by visiting sites in person
• When you look at the critical data, think about how it differs over time and between groups of people in your organisation (eg junior versus senior staff), and how the issue affects competitors
• Make a ‘causal map’, using Post-it notes to describe each crucial piece of information, and see if you can spot any patterns by visualising it this way

Build an imaginary council

It’s also vital for entrepreneurs to have mentors, peers or friends who they know will see things differently to them, advises Webb.

You can run ideas past them and they will challenge you.

“You don't even actually have to do it in person,” says Webb. “I encourage all of the people I work with to have a little council in their mind of wise people.”

For one of the CEOs she coached, it was “a really good old mate who he knew would tell the truth”.

How to delegate effectively

An effective team brainstorm may reveal a bold new strategy for the business to undertake. To execute this, the founder will then need to delegate effectively. But this doesn’t always come easily.

“We want to keep hold of the things that we used to be good at,” says Webb. “It's natural. If you're the founder and it's your baby, it's hard to let go of what you used to do, that you know got you to where you are now. That is a big identity shift for a lot of leaders.”

When a business is scaling fast, it can feel much quicker to do things yourself, so holding on is rational in the short term.

But there’s a deeper psychological fear at play, says Webb. If founders hand over responsibilities to colleagues, the thinking goes, “they won't do it the way that I want them to do it”.

The founder loses control and autonomy.

The power of autonomy

It’s very important to set out “clear expectations” when you delegate, says Webb. But you must also take care to leave space so “there's room for colleagues to grow, explore and experiment themselves. Autonomy is such a deeply motivating force in humans.”

The thing you fear losing yourself, autonomy, is what you have to ensure that you give to others.

To appreciate this, just think of the opposite. Imagine an overbearing boss constantly leaning over your shoulder and saying, ‘you missed something'.

“This not only makes you feel like you're perhaps not as competent as you thought you were,” explains Webb, “but it also annoys you pretty quickly!”

The Fix-Flex approach

On the other hand, Webb acknowledges, you do need to make clear that support is available when you delegate.

Webb recommends the ‘Fix-Flex approach’. This involves deciding beforehand where your views on the deliverable are fixed and where they are flexible. When you have a non-negotiable in mind, say so directly, for example, “This is where I have a clear view…”

Being open about your boundaries when you delegate gives people a sense of structure and shows them where they have freedom. You might let them decide on the format, timing or content of a presentation, for example.

“You're really trying to find the right middle ground between micromanaging,” says Webb, “and saying, ‘I trust you and I'm just chucking it over the fence’. It's a balancing act. It's a different hat to put on and as entrepreneurs, you have to put on so many hats.”

Caroline Webb's four lessons for leaders

Assume you’re missing something. Webb’s starting point for strategy is accepting that your brain shows you only a fraction of the picture. Set your own view aside, assume you’re wrong somewhere and get curious, swapping confrontational questions for coaching ones such as ‘What’s your hunch about what’s going on?’

Make it safe to speak up. Reward openness even when the news is bad, and never shoot the messenger. Silent ‘brainwriting’ before a meeting means quieter team members get their ideas on the table before the loudest voice sets the agenda.

Treat letting go as an identity shift. Holding on to the work that got you here is natural, says Webb, but it can turn the founder into the bottleneck. The autonomy you fear losing is exactly what you need to give your team, because it is “such a deeply motivating force in humans”.

Be clear on what’s fixed and what’s flexible. Webb’s Fix-Flex approach means naming your non-negotiables upfront and leaving the rest to your colleagues. It is the middle ground between micromanaging and ‘chucking it over the fence’.

Leadership Intelligence is published by Macmillan Business and is available now.