Having a Difficult Conversation? Try being an Advocate.

While no single conversation is guaranteed to transform a company, a relationship or a life, any single conversation can.

Susan Scott, best-selling author (Fierce Conversations — Achieving Success at Work and in Life, One Conversation at a Time), Fortune 100 public speaker, renowned leadership development architect, global business community thought leader

Difficult Conversations 2014-02-18

Image by Edwin Lee

When I have to deliver a tough message, my first inclination is to vent my frustration with the situation by telling that person how he messed up production and/or alienated his team. However, while I would walk away feeling vindicated, I also knew I would accomplish little to improve the situation.


  • When leading a post-project review or performance appraisal, how often do you express frustration at your members?
  • How would the performance of your team be different (in the foreseeable future) if you exercise the role of an advocate (instead of a disciplinarian or instructor)?
  • Emotion is a double-edged sword. Does your tone of voice present you as approachable & caring?
  • How can you & your audience design reward(s) and focus peer accountability to achieve the improvement plan?

Providing difficult feedback is never easy. No one looks forward to hearing about how he failed in a particular effort. For the most part, no supervisor looks forward to communicating that message! More commonly, supervisors feel just as uncomfortable giving the difficult feedback as the recipient does getting it.

Is there a way to relay difficult messages without alienating the other person or diluting the importance of the message? Yes, take the role of advocate. You’re having this conversation to make things work better for everyone, including the recipient, right? Rather than being the disciplinarian, be an advocate – wanting what’s best for the future successes of this person. And in this role, focus on helping the individual: advance skills, improve habits or even situational changes that could result in a better outcome, improved delegation skills, more authentic communication, or even mitigate work-related obstacles.



Prepare. While the importance of reflecting on the conversation (after the event) is noted, it is equally important to spend time preparing prior to the conversation.

Check Your Own Frustration at the Door. This conversation needs to be about the growth of the person receiving the feedback. Venting your frustrations or conclusions may make YOU feel better, but will more than likely trigger defensiveness in the other person.

Acknowledge Emotions, Both Theirs AND Yours. Acknowledge that it’s hard to hear this type of message… and that it’s hard to give it! Express (if it’s true) your deliberations over how to have this conversation because you wanted them to feel comfortable talking with you about it. Opening the dialogue this way, helps the recipient prepare for a difficult message and may actually lessen the blow.

Just the Facts, Ma’am. Calmly communicate only facts that you have observed or those which can’t be disputed (e.g. I noticed that you have arrived late all week, the proposal had several errors, the deliverable is three days late), rather than what others thought, the given impressions, or how you felt.

Encourage Reflection Through Questions. Once the facts are on the table, it is important that the person own the problem – and the solution. Rather than “telling him” what to do, ask him– what could be done. Asking mindful questions helps your audience see the problem more clearly and makes the solution more concrete for them. Ask: “If you had a do-over, what would you have done differently?”, “What should have happened that didn’t?”, “Who can help prevent this from happening in the future?” These questions create ownership, allowing the person to formulate his own realistic solution.

Help Create an Achievable Action Plan. Openly play devil’s advocate – asking questions about what might sabotage her plan – what could go wrong? Inquire on her mitigation plans – what could be done? Can she sustain her actions long term?

Don’t Forget The “How”. Make sure both of you understand HOW the plan will happen. Getting to work on time may be the right solution, but HOW it will happen is where the improvement begins. Can you walk me through this plan? Who needs to give you buy in? What will you say to them? How will that go? The plan then becomes do-able.

Keeping The Goal In Sight. Be empathetic, but don’t get side tracked by emotions or circumstances. Calmly circle back to what you need to happen until a solution is found, “I can understand your dilemma, but I need you, and your team needs you to …let’s focus on how to make that happen.

When the conversation is over, take a moment to reflect on how YOU did. What could have gone better? What worked for you? It will never be easy, but learning even a few of these strategies, can turn difficult conversations into learning conversations that set the path for more engaged employees and sustainable success for everyone!

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DeAnna Myers

1 Comment

  1. DeAnna – nicely done! Your insights are helpful and provide ideas we all can use to become better advocates. – Sandy

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