How Executive Coaching Can Help Leaders Who Have Trouble Delegating

One of the most common development challenges we encounter as executive coaches, particularly when being asked to work with mid-level high performers who have recently been promoted to lead a team, is the ability to delegate. Often characterized as “micro-managing,” a reluctance to delegate has many implications - not only for the success of the leader themselves, but for the culture and effectiveness of the team and the organization. Here’s why:

Why is Delegation Important?

One of the things I will often say to leaders who struggle to delegate is “If you already know how to do it, someone else should be learning it.” What that means is that a leader’s real job is not actually to “get the work done” but to build the capacity and capability of their team by ensuring everyone is learning and growing (and to “use” the work to stretch and grow and develop the people). If the leader isn’t delegating they are missing an opportunity to teach such that someone else builds a new skill or area of expertise.

The other reason delegation is important is that teams are created where the workload and requirements are greater than any one person can deliver. The more tightly a leader holds on to an array of tasks, the less overall capacity can be leveraged from the team. In essence a poor delegator is robbing the organization of critical capacity.

Finally, organizations need leaders who can look beyond the day to day tasks and set vision, devise strategy and foresee future opportunities and risks. If leaders at all levels are buried in the day to day of the business no one will be holding that future vision and charting that course forward.

Why do Leaders Struggle to Delegate?

We find this often when a leader has risen through the ranks of their function or area of expertise - they have a belief about how things “should be done.” (Coaching tip - the word “should” is an immediate red flag). Their perspective tends to be that doing the work “their way” was what helped them move upward - therefore their way MUST be the “right way.”

We hate to break it to you, but there are very - very - few things in this world where there is just one right way.

The fastest way? Sure. The most error-free way? Maybe. The most cost-effective way? Most likely. But the “right” way? Rarely.

Ascribing a “right” or “wrong” to any one way of doing things presumes that there is no room for learning, for evolution or for innovation in the doing of whatever it is. Not to mention that - another of the things I find myself saying quite often - if the individual needs it done “their way” - they are going to have to do it themselves.

Another barrier to delegation is lack of trust - if the leader doesn’t trust that their people can do the work they may hang on too tightly. Rather than address the skill or capability problem a solution-oriented leader will default to “I’ll just do it myself.” After all, that’s a lot easier than giving someone difficult feedback and engaging in developmental coaching and/or training, right?

And then there’s “perfectionism” - a sneaky substitute for what amounts to a high need for control. Similar to the idea of “right,” perfectionism is a largely unattainable goal whose spectre looms large as the threat of failure, embarrassment or risk to job security. Not to mention that not everything requires anything close to whatever “perfect” might be perceived to be.

How Can Working with an Executive Coach Help a Leader Who Struggles to Delegate?

Executive coaching is a personalized, one-on-one leadership development approach that enables a laser focus on specific challenges. In a trusted, transparent coach-client relationship there can be open conversation about what a leader believes about their role, their own ability to be successful, and about their team members.

One of the biggest benefits of working with a coach is the coach’s objectivity. Or, as one friend of our firm likes to say, “You can’t read the label from inside the jar.” A coach can listen to how a leader is approaching their role and make observations, identify disconnects or inconsistencies, and challenge points of view and perceptions that might be impeding a leader from trusting what others can do.

An executive coach will invite a leader to reflect on their current approach and assess the degree to which it’s supporting the achievement of the desired outcomes. Coaches focus on learning and observable results, and challenge the client when “walk” and “talk” are not aligned.

The coach might suggest the leader ask for feedback from their direct reports. They might suggest role playing. Or they might set some modest targets for new behaviours that they can debrief afterwards. They might also bring examples from other leaders with whom they’ve worked and who’ve had success dealing with a similar challenge.

Benefits of Improving Delegation Skills

Employees who are challenged, who are invited to grow and learn and who are trusted with increasingly difficult or complex tasks are more engaged. That means that the individuals and the team all perform better. More capacity results in more satisfaction.

Leaders who delegate effectively are less likely to suffer from burnout. There are fewer better recipes for exhaustion than consistently trying to do too much. Their decision-making benefits from clearer thinking and they are better able to think and act strategically as opposed to tactically.

Longer term, a leader who is seen as being able to build capacity and capability is seen as a leader who is an asset to the business, and therefore more likely to be able to handle higher level and more complex responsibilities. Delegating skills are critical to career advancement.

An Example

Melissa runs a large client group for an advertising agency. She’s trusted by the client and well-liked by her team and colleagues. Yet she consistently works evenings and weekends and often describes herself as being “pulled in multiple directions.”

Melissa’s coach challenged her idea of what it takes to succeed - noting the frequency with which she talked about “having to step in” and “helping” her people. She believed it was her responsibility to have a close eye on all of the work being produced by her team, and was reluctant to risk “upsetting” her people by overloading them or challenging them to the point of discomfort.

What Melissa had missed out on was the opportunity to instill in her people the understanding that it was their responsibility to flag risks to deadlines and deliverables, their job to assess their workload and their role to identify when an assigned task was truly beyond their abilities or just “stretch-y” enough to be uncomfortable. Melissa liked being liked and had conflated being “nice” with being an effective leader.

A few discussions about her beliefs and assumptions as well as some guidance from her coach with regard to how to have developmental and accountability conversations with her people and things got a lot better. Melissa’s direct reports had more access to more challenging work, Melissa learned to let them run with a project until an agreed upon check in point, and everyone - Melissa included - learned that a little discomfort is necessary for growth and learning.

Wondering How You Can Improve Your Own Ability to Delegate?

Take a look at the moments when you are tempted to step into something assigned to one of your direct reports. Is the project really in trouble or are you “just interested?” Do you actually need that data or would you just like to know what’s going on? And most importantly - do you trust the individual who’s got responsibility for the work? If you do, let them run with whatever it is you’ve assigned them. If you don’t - either support their learning and growth or make a change. It’s not healthy or helpful to keep team members who aren’t capable of doing the necessary work at the appropriate level.

Ready to improve your delegation skills and become a more effective leader? Consider working with an executive coach to unlock your potential. We are always happy to have an introductory conversation.

Reach out to us at info@parachuteexecutivecoaching.com