The fear of difficult conversations

Shai Haddad
3 min readSep 29, 2019

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A lack of managerial courage may be hurting your business.

The fear of difficult conversations has been plaguing leaders for decades. Managers postpone, or even worse, avoid conversations around performance, work ethic and accountability. The root cause can vary, from our cultural norms surrounding what we consider “being nice” to a lack of management experience, or simply a lack of courage. Avoiding difficult conversations leads to a lack of clarity at first, followed by reduced engagement and decreased trust. Ultimately, the result is the absence of accountability and failed execution of a potentially well-planned strategy. Needless to say, the impact can be hard to reverse.

Great companies with extraordinary talent and innovative products may be failing simply because their internal leaders are not equipped to effectively deliver difficult feedback through tough conversations. It is a core element of building high performing teams and yet so often not prioritised.

Some managers avoid conflict and instead focus on “areas of improvement” mainly because it makes them uncomfortable…but what is comfort if not an obstacle to growth? The truth is, no matter where you are in your career or life, receiving negative feedback is never fun. But without it… we cannot grow. Think about this scenario — no one gets fired and says « thank you for NOT addressing this issue with me ». If you truly care for your team, you will address concerns. How can we get better at having difficult conversations?

Here is what has worked for me over the years:

1. Common goals

For honest feedback to be received, understood and acted upon, you must first have a common goal. As a leader, have you taken the time to clarify the vision and the journey? This is critical because it sets the tone and helps your conversations be easier to understand and more prone to be acted upon. Moreover, it puts the whole team on the same page.

2. If you are setting high expectations, provide even higher support.

Steve Jobs said: “Some people aren’t used to an environment where excellence is expected”. One of my biggest mistakes early in my career was assuming and expecting a certain level of rigour, resilience and excellence from colleagues and teammates. My journey as a leader has taught me to provide a level of help and support that is even higher than what I expect back. Setting expectations without offering your help on reaching them is a shortcut to failure. Leaders must make sure that they set high expectations while they are offering an even higher level of support. How often do you meet with your team? Are you actively asking what they need help with? Do you make yourself available to them? Try it. I was amazed to see how much more we accomplish as a team, when there is extensive support from leadership.

3. Build relationships

Imagine having a difficult conversation with a new team member that you barely know. How do you think it would be received? It is unlikely that the message will be understood or sincerely listened to. A leader must invest time and care into getting to know their team. How else would you know their aspirations, motivation, triggers? This is a vital part of your journey as a team towards true engagement and trust.

In a nutshell: you can care and value an individual while also raising areas of concern. If you are praising achievements and celebrating successes regularly, you will also be more successful in providing constructive feedback. This becomes even more effective when you create a structured and regular feedback environment. It makes the difference between providing an “evaluation” VS providing an opportunity to “learn and grow”.

I would love to hear about your experiences and thoughts on this topic. How can we get better and more courageous?

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Shai Haddad
Shai Haddad

Written by Shai Haddad

Former rapper turned Growth strategist. Still Learning. I am driven by a passion for people, technology and efficient processes.

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