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Addressing Common Leadership Issues - Pt3: Difficult Conversations

Updated: Aug 23, 2022

This is the third in a series of blogs in which we will look at some of the common issues faced by modern leaders and how they can be addressed. Today, we will consider how to approach difficult conversations.

Difficult conversations are a necessary part of leadership. However, many people find them very stressful and best avoided where possible. The main reason for avoidance is fear. Often, it is a mix of fears about:

  • How they will react

  • Being wrong

  • Consequences of confrontation

  • Hurting their feelings

  • Not knowing how to approach it

  • Previous bad experiences

  • Making things worse

  • Etc.

However, avoidance will never yield the change you are seeking. One of the key traits of effective leadership highlighted in my LinkedIn article ((3) What the Best Leaders do Differently | LinkedIn) is 'courage', i.e., a willingness to do what is right, not what is easy or popular.

So, how should such conversations be approached? Just take a 'brave pill' and charge in? No. The good news is that there are things you can do to make such situations more manageable and more likely to generate the desired outcomes. Here are some tips:

1. Change your mindset.

If you are already convinced it is going to be an unmanageable or very difficult conversation, it is more likely to be so. Try to reframe positively. For example, if you have to give negative performance feedback, think of it as a constructive conversation that will help them develop. If you have to say 'no' to your boss, think of it as offering an alternative solution instead.

It can also help to visualise the consequences of avoiding the conversation, for them, the organisation and yourself. This will help it seem less daunting.

2. Prepare.

Think about why the conversation is necessary and what you want to achieve. Articulate your answers to questions such as these:

  • Is it necessary?

  • What would happen if you did not have the conversation (including impact beyond the immediate parties)?

  • What does success look like?

  • What has been done already and what happened?

  • Where are we starting from?

  • What steps could be taken to move in the right direction?

  • What could prevent progress?

  • What style should you use (consider their SDI2.0 profile (see below) and frame your approach accordingly)?

  • How are they likely to react?

  • What questions/objections are likely to be raised?

  • Etc.

Articulating answers to questions such as these, and perhaps discussing them with a coach, will help ensure you have a clear idea of how the conversation should be conducted and what success looks like. The answers will give you a framework to guide the discussion. This step alone will give you more confidence. However, do not script: if you do, you are more likely to come across as less authentic.

3. Choose an appropriate time and place.

If the issue is sensitive and important to either you or them (or both) show that you are taking it seriously by finding a time when you can both meet without distractions and in a place where confidentiality can be maintained.

Allow sufficient time for the meeting not to be rushed, but do not make it too long - discussions can all too easily expand to fill the time available.

4. Control the meeting.

Start and finish on time whenever possible and ensure your phones are off.

Ensure you keep the discussion on track. If unrelated issues arise and threaten to derail progress, put them aside to address later. Paraphrase periodically to show that you are listening and ask them to do the same.

Be honest and authentic. Flexing your style to better communicate with others is another of the key skills identified in my LinkedIn article (above). In doing so you are not changing yourself or compromising your principles, you are demonstrating relationships intelligence (RQ) to help them improve. Don't worry about being liked: your aim is to be honest, fair and clear. That is the best service you can provide for those for whom you are responsible and the vast majority will respect you more for being so.

Keep your cool and keep it about the facts. Be prepared to back up any critical feedback with clear examples to illustrate your point. If they get very argumentative or emotional, e.g., start crying during a bad performance review, do not buckle or apologise: silence will often be a calming influence. If necessary, consider taking a short break. If they are unresponsive or very hostile to your approach, professional mediation is an option to consider.

Be clear but compassionate. They are the focus, not you. Do not try to arouse their sympathy for you by saying things like "I wish I didn't have to do this."

Pre-empt likely objections and blame-shifting by using 'and'. For example, 'and I know you worked late', or 'and I know you are new to the team', etc. before they can raise the point.

Be reasonable. If they raise good questions or counter-evidence, acknowledge their validity and be prepared to investigate further or change your course.

Check their understanding of what is required before closing the meeting. It is a common mistake to try to rush to the end and assume they are as clear as you about what must change. Get them to spell out what they will do differently and when.

5. Follow up after the meeting.

Capture the key thoughts, decisions and actions that arose, and put checkpoints in your diary to verify progress.

Take time to review your performance as well. What did you learn? What went well that you could do more of? What could have been done/phrased better and how?


If you dislike difficult conversations you are not alone! However, they are often necessary for effective leadership and they can become easier with an informed approach.

The keys are to have a positive mindset, to be prepared and to remind yourself of the consequences of ducking the issue.

A fundamental part of the preparation is to understand their motivations and reactions to stress or conflict. Tools such as SDI 2.0 are a real help here as they surface motivations, how they react to conflict and their preferred behaviours (strengths). Knowing this information makes it easier to develop RQ and facilitates their engagement with the changes required. A sample report is attached to show how this works.

Difficult conversations may never be a pleasant prospect but, by following the tips above, they will become a bit easier and more productive. Handling them in this way will promote better outcomes with less pain for you and for them.

If you have additional tips that could help others facing this issue, please add them to the comments.

Aspire MCL's principal consultant, Ian Kirkby, is a certified SDI2.0 facilitator with extensive experience in developing high-performance leaders and teams.

Take the first step to unleashing YOUR leadership potential: get in touch today by emailing or calling on 020 3904 7501.

As noted above, this is the third blog in a series addressing leadership issues. If there is a topic you would like Aspire to cover in subsequent releases, please comment or email We will not spam you!

Aspire MCL: Leadership problems - sorted!

SDI 2 - Sample - full-victoria-patel-sdi2-personalized-report-2020-07-30
Download PDF • 5.14MB

Further reading:

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