The Top 5 Leadership Obstacles and How a Coach Can Help

We asked our coach and resident leadership expert Dan Crompton to share what he’s learned coaching over 50 CEOs 1-on-1 over the past half-decade. Here, he describes 5 of the major obstacles in leadership and management that he sees people grappling with and explains how a business strategy coach can help.

Obstacle 1: Communication Breakdown

The presence of power difference and hierarchy has a big influence on how easily and effectively people feel able to communicate. For instance, most people find it unusual at first for their manager to ask them for criticism and feedback.

“Because of that weird reaction to hierarchy,” Dan says, “you don’t always get honest feedback. You don’t always get a true sense of what’s going on within the team or how things could be done better.”

It’s something that flows both ways – leaders often feel just as uncomfortable giving their staff the constructive input they need to improve. Whether you’re afraid of damaging someone’s confidence or fearful of a messy confrontation, it can be very tempting to put off having difficult conversations. In a survey by Zenger Folkman, 21% of managers said they avoided giving negative feedback entirely!

A business coach can help put systems in place that make feedback much less daunting for everyone – for example many of our clients run 360 feedback mornings every 3-12 months.

“Some of the work that I’ve been doing with both leaders and teams is on how to create a culture where feedback is a good thing. So everyone, regardless of level, feels comfortable giving it,” Dan explains. “That feedback just becomes a norm of how you communicate, not something that’s just asked for in an online survey once a year.”

They can also provide frameworks to help leaders approach those challenging conversations. Dan is quick to point out that difficult conversations are always going to be difficult. However, having a framework to follow means that topics get addressed, rather than getting ignored.

Obstacle 2: Delegation and Empowerment

Dan believes there are two major issues here.

Firstly, it’s very difficult for a leader to relinquish control and allow other people to act and speak for the business that they’ve built from the ground up. The second problem is that even when leaders do feel able to delegate something, they usually don’t have the systems in place to allow their staff to take full ownership of the task.

“There’s a big difference,” Dan says, “between delegating a task, which is what most people do, versus delegating responsibility for that task.”

When you only delegate the task itself, the responsibility for it remains with you. It keeps taking up valuable mental bandwidth because you’re still having to ensure it’s done well and that any issues get addressed. A business coach can help with both of these problems. First, they can work with a leader to work through their feelings about relinquishing control. Then, they can ensure that there are processes in place that will make delegation truly effective.

“There are four steps to delegation and most leaders only know the first one,” Dan explains. “You need to explain what needs doing; why it needs to be done; provide the necessary training and resources; and finally ask the new task owner to summarise and reflect back what they’ve heard to test their understanding.”

Obstacle 3: Managing Change

The overarching issue here, Dan believes, is that nobody genuinely likes change.

For leaders, it can be very demoralising to accept that the way they’ve been doing things isn’t working and that they’ll need to start from scratch. For teams, change often feels like an arbitrary thing that’s being inflicted on them from above. The way they’ve been doing things (perhaps for a very long time) is being disrupted and they’re being forced through an unnecessary adjustment process.

A different but equally problematic situation arises when a leader is too focused on change and flits from one new initiative to the next, something Dan terms “shiny object syndrome.” This can lead to a team developing change fatigue.

“Where we come in as coaches is to help business owners be really clear on their strategy,” Dan says. “So yes, that means change, but not constant flip-flopping and changing from one thing to the next to the next.”

Rob Whitlock highlights this process in his 5-star Google review of our group coaching program: “For me the most significant change in my mindset as a result of undertaking this course is to try and think more strategically. I now try to see the bigger picture and not make changes in isolation.”

A coach can also work with the team by helping to facilitate workshops. This gives the leader a chance to explain the rationale behind the process and to get input on how best to achieve the goals, giving everyone that all-important sense of ownership. “The earlier you can bring a team on to at least be part of shaping that change,” Dan explains, “the more likely they are to be on board with it.”

Obstacle 4: Vision

Leaders often underestimate the important role having a strong company vision can play.

Even if a leader knows exactly what they want their company to stand for, they may struggle to communicate that to their team. Because the abstract language used in many vision statements is often completely detached from people’s everyday experience (“responsibility, quality, excellence…”), staff tend to see the principles as nice-to-haves at best or meaningless fluff at worse.

As Dan explains: “It shouldn’t just be a kind of notional idea that appears on a website or in an employee handbook. It needs to be something that’s actually meaningful, that the team is behind and that influences their day-to-day work and how they behave.”

Thinking about how a coach can help to make this a reality, he suggests: “I think our role here is to run workshops and away days to help the whole business understand why the vision is important: why it actually matters, both internally as a team, but also to the customers they’re trying to help.”

Obstacle 5: Work-life Balance

Dan says he’s never met a business leader who doesn’t struggle with time. “We’ve got clients who are working sixty, seventy, eighty hours a week” he explains.

When you’re a leader, the buck stops with you. It’s easy to feel like working all the time is just the price you have to pay to build a successful business. But this mindset is not only bad for your wellbeing (and by extension your performance), it also causes serious misalignment between your behaviour and your goals. “The reason you started a business was probably to have more time and more freedom,” Dan says, “and yet the reality is often very different.”

Fortunately, Dan says that after a few months of coaching, those people working 80 hours a week can get their evenings and weekends back. That’s because a coach can help a leader to properly value their time and define which tasks they should prioritise. And while the strategies and techniques covered do help people manage the time they spend on their business, they also apply to their personal lives as well.

As Dan explains: “You’ve got to be almost as rigorous with carving out time for your personal stuff as you are with managing your Monday to Friday calendar.”

Final Thoughts

Communication issues, ineffective delegation, poor change management, a lack of vision, and no work-life balance – these top leadership challenges can hamstring even the most talented leader. By helping to transform the company culture, getting you and your team on the same page, and putting robust systems in place, a business coach can help you dismantle these obstacles.

If you’d like to find out how a coach could help you tackle the challenges you’re facing as a leader, book in for a free 45-minute coaching session. You’ll receive advice tailored to you and your business, as well as practical strategies you can start using right away.