Delegation and how to do it successfully is a perennial problem in business. I would be surprised to find anyone who hasn’t found it a challenge at some point in their working lives. In my executive coaching work, I find it to be particularly problematic in smaller, entrepreneurial start-up companies, especially when they’re growing.

There is, of course, a plethora of resources on delegation techniques and methods available, so it is not my intention to tell you something that merely regurgitates what’s already out there. That’s probably not what you’d need anyway, so I thought I’d provide an alternative option that you could find of value.

I will also explore key areas my clients and I have found valuable in helping them to get their heads around letting go and delegating in ways which work more appropriately for them and their team/organisation.

What is delegation?

First we need to ask ‘What does delegation mean?’ This may sound like a silly question, but when I explore this concept individually and within teams, we can arrive at some pretty interesting places – sometimes very different ones too.

Traditional delegation is typically a top-down management approach which harks somewhat back to the industrial era. The boss passes a piece of work on to a subordinate, defined by some parameters, for a purpose and defined output. Unawares to all parties involved, this usually comes with a whole host of undefined, undeclared, and un-communicated (some of which are probably un-communicable) assumptions and expectations. And therein begin the problems.

The issues are usually compounded by the boss retaining ultimate responsibility and accountability for the work. With entrepreneurs and small business owners it’s further compounded by their often intimate relationship with the business. In many cases, but by no means all, the delegate does not have the same vested interest in the business either.

“Delegation is often seen as more of a one-way street from superior to subordinate, which means organisations can miss out on potentially valuable input”


Unpicking the variables and avoiding deviations in any work delegated in this way can be a messy task. It can also take a lot of time and effort.

Delegation is often seen as more of a one-way street from superior to subordinate, which means organisations can miss out on potentially valuable input from that subordinate which can then reduce both productivity and creativity. It can be quite ineffective in many organisational contexts too.

So what needs to change?

It’s a relationship of sorts

When working with leaders (e.g. entrepreneurs, founders/cofounders), I find it common that the quality of their relationship with the business is a stumbling block to effective delegation. It is this relationship that is fundamental to their letting go.

This relationship is, of course, a fluid and dynamic thing so it isn’t about a tweak here, or fix there, it is an ongoing process of engagement which necessarily involves a certain amount of reflection and self-awareness about how they bring themselves to their role.

Delegation is not black and white:
For example, when I was working with a company founder recently, we were exploring some frustrations he was experiencing. He desperately wanted to be working more at the strategic level of the business but was finding himself constantly drawn back to solve critical operational problems, despite having delegated the responsibilities to a team. It just wasn’t working and it was wearing him down.

As we explored the nature of his frustrations, all the approaches he had used to resolve the issue, including training and consultancy, a pattern around how he viewed his connection with the business emerged.

Whenever we touched upon the process of stepping back and trusting the people in his team (despite his reservations) he alluded to not being at a point where he wanted to leave the business. I reflected this back to him and as we discussed it, a pattern in his perspective emerged: that if he steps back it means, however irrationally, literally turning his back on, or completely losing, the business. It was black and white.

Moving beyond this realisation allowed us to play around with some ideas about the origin of this and how it related to previous professional experiences, but, more importantly, it gave us the opportunity to consider the process of letting go as a movement through many different shades of grey.

The quality of his perceived connection with the business and relevant team coloured the delegation process, but what also transpired were his standards and expectations around the outputs that could never be delivered by the team because they were based upon how he would do it. These expectations are, of course, something that nobody else is ever going to live up to, especially if it involves something as complex as the development of a revenue generating unit.

This introduces the next key relationship, which is with the delegate or delegate team. Within the traditional model of delegation, this is again viewed as a transaction where the superior provides the parameters. The person of the delegate doesn’t seem to come into it much. However, from the perspective I’m introducing here, it would involve a mutual nurturing and fostering of a co-operative relationship, which to an extent turns the process on its head.

I appreciate that the idea of trying to go through life and work unpicking the flow of things in this way would seem a bit overwhelming and leave little time for anything else, but we can find another way of doing this that makes things easier for ourselves. And frankly, I find it invaluable in dealing with the natural complexities of people and business.

The central status of the delegation relationship

In the context of letting go and delegating, what matters and makes interactions meaningful are the qualities, or characteristics, of the relationship between the people interacting – not the people in and of themselves.

I think it is important to highlight that those with the seniority in the process need to have some awareness about how they might be seen by those they’re delegating to. It may be that you think you run a flat organisation without a hierarchy, but is it really a non-hierarchy and does everybody in the organisation see it, and you, in that way?

Is it collaboration or cooperation?

I personally think that whether you think of delegation as collaboration or cooperation is important:

Collaboration is an emergent subject in the world of business for many reasons. According to the Oxford Dictionary of English, collaboration is defined as ‘working together with someone to produce something.’

For the purposes of delegation, it could very well fall under collaboration but I view it more as a co-operative process as it is about ‘working together to the same end’.

Some learning and how to

office-discussion-shutterstock_526395022When you are in a leadership role, the key principles of learning to delegate come about by making delegation a process of inquiry which both shares and co-operates in the work needed to be done: imagine approaching it is as if you are nurturing a new relationship which requires getting to know the person you’re going to be working with. Both the extent and complexity of the work that you delegate will naturally move along a continuum that develops as the relationship grows, but bear in mind that it may not do this in an entirely linear way for either of you.

You begin by accepting the person you are delegating to is a unique individual able to bring their personal value in their own way.

Articulate what you need to do in terms of the intended outcomes and talk to them to arrive at a place where you agree what that outcome should be. Enter into it and explain it as a shared task that you’re both working together toward achieving, inquiring into their perspective, imagery, opinion and input into what they feel they could do to provide most value to the task at hand.

Explore what part of the work they would like to take on and what motivates them to do this. What do they see as their strengths in doing this and what do they feel will be the extent of your input/support, if any at all? How would they propose doing it and how do they imagine the outcome?

“As leader, you need to put aside your expectations and ideas about what you think the outcome should look like”


The most challenging task here is probably for you as leader, to put aside your expectations and ideas about what you think the outcome should look like, including what you think they should be doing and how.

If what you’re doing is simply comparing what you would do with what they’re proposing it’s not likely to have a lot of success. Indeed, by acknowledging the importance of their input into the process and allowing for it, you’re much more likely to open the door to unique and novel input from them that you may not have thought about, or imagined. You allow for their creative input to feed into the process.

This compartmentalisation can be difficult because it demands an in-the-moment awareness, checking of our own thoughts and actions. It also includes briefly suspending them to allow more space in the conversation and therefore an improved likelihood of a mutual understanding and direction.

The helpful side of this kind of conversation is that you’ll naturally tend to become more aware of the extent of what your input may be – so you’re not hit with the surprise of having to do it all yourself at a later date.

Because you’re not just handing something over following a bit of a briefing and you’re learning a new approach, it may, to begin with, necessitate more attention on your part. But you might just find yourself with some progress, step by step, that builds trust and reduces your anxieties about progressing the delegation of tasks and responsibilities within your organisation. It becomes an ongoing learning process of your employee and organisational capabilities which in a sense improves your relationship with the business, perhaps informing how you bring yourself to your role too.

You can find out more from Simon Darnton at his website or by following him on Twitter here: @SimonDarnton

Simon Darnton