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Leadership Improvement Areas - Main

There are many ways to improve as a leader. But what are the leadership improvement areas that are most applicable to thoughtful leaders?

In this article, I take a look at the most common leadership improvement areas that I see, based on working with my coaching clients and responding to lots of questions!

I’ll also propose some ways to try to work on these leadership improvement areas and make real progress.

Thoughtful Leaders and People Are a Good Fit

Since I created the Thoughtful Leader website in 2015, I’ve spoken to a lot of thoughtful leaders. I’ve answered a lot of questions from thoughtful leaders too.

In general, what I’ve observed is that thoughtful leaders don’t really have an issue with taking time to think about the people they lead.

Often, thoughtful leaders have a strong sense of empathy, being able to consider situations from another person’s perspective.

This makes for good leadership, in my view. When you work for someone who takes time to consider the impact they have on you, you’re likely to feel respected. You’ll be more likely to trust that leader.

While this empathy can be a great advantage, it comes with its challenges too. And that’s where a lot of the leadership improvement areas lie for thoughtful leaders.

Learn More:  4 Ways Leaders Can Build Empathy in the Workplace (and Why It Matters)

Leadership Improvement Areas for Thoughtful Leaders

Let’s take a look at some of the areas where thoughtful leaders can improve their leadership.

Obviously these won’t apply to everyone, but these are the common areas that I see that might be worthy of your focus and attention!

Once I’ve introduced these leadership improvement areas, I’ll also look at some ways to motivate yourself to take action on them.

1. Pushing Back or Being More Direct

Many thoughtful leaders don’t enjoy conflict, myself included. This comes from having a tendency to like people working together in a harmonious and productive way.

In general, thoughtful leaders like people to get along. They like to be agreeable and to help others.

However, this helpfulness can cause problems, such as:

  • Not saying the things we really should be saying, because we’re being too nice
  • Taking on too much work, for fear of upsetting someone by saying “No”; or
  • Putting ourselves last, and everyone else first, because we’re trying to be too helpful.

Pushing back takes courage and saying “No” can be uncomfortable.

However, I see many problems arise in organisations because people are saying “Yes”, when they want to be saying “No”.

Chaotic work environment - pushing back

How to Push Back More Effectively

Pushing back is a critical skill for leaders, and it doesn’t necessarily mean being unhelpful.

There are different ways to go about it that can result in a positive outcome, without causing a huge amount of conflict. You won’t always succeed at pushing back, but you never will unless you try.

Here are some resources to help you push back more effectively:

However, one of the biggest challenges I see thoughtful leaders facing is not that they don’t know how to push back.

Instead, it is that they need to feel more motivated to push back. They need to feel like it’s worth the trouble. I’ll cover this a little later in this post.

2. Holding People Accountable

Thoughtful leaders know they need their people to do good work for the team to succeed.

Part of this is making sure that each team member is performing, and making sure that people are behaving in a respectful and constructive way.

Holding people accountable is an extremely important part of team performance.

And nothing annoys high performers more than seeing other team members “get away with murder”!

Accountability involves clearly setting expectations, monitoring performance and then making sure there are consequences and rewards that reinforce those expectations.

You can learn much more about this topic in my online course: The Team Accountability Builder.

The course not only covers the steps involved in accountability, but also how to create the right environment for your people, and map out a plan to improve it in your team.

So why do thoughtful leaders struggle to hold people accountable?

Often it’s because holding someone accountable may involve having an uncomfortable performance conversation or feel as if you’re picking on them.

Once again, it’s the common problem of being “too nice”. You can find some more resources to help with accountability below.

Learn More:  Can’t Hold People Accountable? Here’s Why

Learn More: Thoughtful Leader Podcast #161: How to Improve Accountability In Your Team.

Learn More:  4 Ways Leaders Damage Accountability in the Workplace.

3. Delegating More

Many leaders can benefit from delegating more, which is why it’s one of my top leadership improvement areas.

However, thoughtful leaders can suffer from this problem more than other leaders.


In some cases, I’ve found that thoughtful leaders feel bad pushing work onto their team, especially if the work isn’t very exciting.

At other times, I’ve noticed that leaders feel as if they should be “sweeping the sheds”. That is, that they should be taking on lower-level tasks to show they are not “too important” for them.

And yet another situation I see is when a leader fails to delegate because they feel more in control when they can do all the work themselves.

Delegating tasks

Obviously failing to delegate causes problems.

You might take on too much work and become overwhelmed. Or, you may actually spend time on low-value tasks that don’t make sense for a highly paid leader to do.

But ultimately, failing to delegate can mean that you are depriving your team of opportunities to learn and grow. To try new things that are a step up from what they normally do.

Here are some resources to help you, if you’re struggling with delegation.

Learn More: Thoughtful Leader Podcast #18: How to Delegate to Improve Your Team.

Learn More:  Too Important For That Task? Is It Good or Bad Leadership?

Learn More:  Why Leaders Don’t Delegate Tasks (and How to Fix It).

4. Focusing On Your Own Wellbeing

The final leadership improvement area I’ll cover in this list is all about wellbeing.

I’ve always been a strong advocate of looking after yourself, before you can help others.

This is one of the important principles that underlies my own coaching.

If I’m not sleeping well, feeling unhappy or stressed, I won’t be able to coach my clients effectively. If I’m not improving my own wellbeing and state of mind, I cannot expect my clients to bother improving their own!

Wellbeing is a Choice

That’s why I think wellbeing is so important.

I could work more, and run around trying to grow my business ever bigger. But in the back of my mind, I know that it needs to be sustainable for me – not something that burns me out.

And so it is for thoughtful leaders. As we covered above, being too nice, avoiding conflict and failing to push back can all cause a problem for our wellbeing.

We take on too much, and fail to speak up when things are unsustainable. Eventually, we collapse in a heap or are simply unhappy, and are unable to support others the way we should be.

Here are some resources for you to focus on your wellbeing, so you can show up the best way for others:

How to Motivate Yourself to Focus On These Leadership Improvement Areas

The leadership improvement areas are fairly clear, but I still see them coming up again and again for many thoughtful leaders.

Motivational Alignment - MountainThe problem often lies in motivation. That is, being able to motivate yourself to take action and make improvements in these areas.

It takes courage to speak up. It takes courage to push back. And it takes courage to hold people accountable with a difficult conversation.

It’s not that thoughtful leaders don’t know what to do. It’s that sometimes, they’re trying to decide if it’s worth taking the step.

I can’t decide this for you, but I can propose an approach to help you decide.

Answer These Questions to Make Progress In These Leadership Improvement Areas

As usual, I like to encourage introspection and taking time to think about our leadership. The motivation to take action lies within all of us, we just need to unlock it.

And you may decide that you don’t need to take action, and that’s OK. The important part is to take time to consciously make that decision.

Here are some of my favourite questions to help you decide whether to take action on these leadership improvement areas.

Q1: “What are the consequences of failing to take action?”

Recent neuroscience research has shown that for motivating yourself, focusing on the potential negative consequences of failure can be more effective that focusing on the goal itself.

That’s what this question does.

What will happen if you don’t have a talk with that disruptive team member?

What will happen if you don’t push back on your boss?

And is the situation sustainable?

Often I’ve found that avoiding conflict in the short-term can result in a much bigger conflict in the future. So let’s try to avoid that, shall we?

Frustrated woman can't Hold People Accountable - Main

Q2: “How do I want to be remembered as a person or a leader?”

Do you want to be seen as a leader who failed to take action when it was needed?

Who failed to hold people accountable?

Or perhaps who was “too nice” at the expense of productivity and performance?

It’s up to you.

Q3: “What’s the benefit of failing to take action? And is it really serving me?”

I like this question, because people often don’t naturally think this way.

When you fail to have a difficult conversation or push back, the benefit might be that you get to avoid an uncomfortable situation, so you feel safe.

When you fail to delegate, the benefit might be that you feel more in control of the work of the team.

If you fail to look after your own wellbeing, the benefit might be that you satisfy other people, even at the expense of yourself.

The next step is to really look at that “benefit” you’re getting.

Is it really helping you? Or is it actually hurting you?

As an example, let’s look at failing to delegate. You feel more in control, which makes you feel safe.

But are you actually creating a situation where your people aren’t learning and you’re piling more work on to yourself?

Over time, you might find that this causes you to have less control because your team can’t do what’s needed, or you become overwhelmed and have nobody to back you up.

Which Leadership Improvement Areas Will You Focus On?

Do any of these leadership improvement areas resonate with you?

Which ones do you need to tackle?

If you need support, I’m always here to help, but getting started means making a decision.

And that decision is up to you.

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