Dreading That Hard Conversation? Take These Seven Simple Steps

Someone on your team is struggling and you’re dreading the necessary, but hard conversation. You care about them and want to handle this with dignity and respect. Here’s what to do.  Assume the best, but prepare for the worst. Put yourself in the best position to both “enter the danger” and “speak the kind truth.”  These courageous dialogues can be career shaping – it can be, and should be, your finest moment as a leader. 

Clearly Identify the Gap

For yourself, make a note of the gaps between the reality of today and your expectations, in simple, factual (not evaluative) terms.  It may help to think of the future, not the past. For example: In the role of COO, I need someone who can provide executive level leadership – hire well, coach well, clearly establish priorities and work collaboratively with other execs on collective results. Today, my operations group is misaligned and has high turnover at the director level. We need more.

Consider the Root: 

Before the conversation, make note of what you think is going on.  This will help you ask the right questions.  In terms of root cause, there are really only three options: 

  1. Willingness (lacks the motivation, confidence, agreement, etc.)
  2. Ability (lacks the knowledge, skill, aptitude, etc.)
  3. Obstacle (willing and able, but prevented by some obstacle.)

Anticipate Reactions:

Before you start the conversation, do some quick scenario planning – how might he or she receive this feedback?  And, what options do you have.  What you are really listening for from them is openness vs. defensiveness.  Reactions might include:

  • The Rejection – “These KPIs are stupid / I never agreed to do this”
  • The Accusation – “Why is this is the first I’m hearing of this?” or “You don’t trust me.”
  • The Explanation – “I’m trying but need more time.” “You don’t understand…”
  • The Defeated – “Maybe I’m not right for this role”
  • The Redirect – “Where is this coming from… who’s been talking to you?”
  • Vulnerability – “I need to level with you… here’s what I’m really dealing with that’s making this hard.  I need help.”

Stay focused on what you know and have observed vs. what others have told you.  Acknowledge the hard work and progress made, but don’t back away from your high expectations.  For example, you might say…

  • “I’ve noticed the tension on the team over this…”
  • “What feedback have you already gotten on this…”
  • “This is not the first time we’ve talked about this…”
  • “Nevertheless, I’m not OK with where we are today… my expectation is still…”

Prepare Options

Think through the options you actually have.  What direction are you prepared to go?  What is on the table and off the table?  Is it ask simple as these…?

  • She stays in role – “this doesn’t need to impact your role, but…”
    • Give her more time / resources – “Let’s give this another month…”
    • Take it on yourself
  • She stays at the company but in a new role – “Perhaps we have you in the wrong role.”
  • She leaves the company – “We can still be friends, but you might not be able to stay here.”

Enter the Danger:

Now the hard part… actually looking them in the eye and starting.

  1. Ask permission.  “Hey, before we start, I’d like your permission to be candid with you about some concerns.  Are you open to me discussing something that might be uncomfortable?”
  2. Be vulnerable and assumptive.  “You need to know, I’m really bad at this sort of thing… giving direct feedback.  But I know you’re mature enough to hear me out and take this seriously.”
  3. Be direct and be brief.  “I want to talk about the KPIs.  There is a gap between what I’ve been expecting and what we have today.”
  4. Name your emotion (vs. acting out of your emotion) – these are ALL important messages:
    1. I’m confused – I don’t understand what’s getting in the way or what to do next.
    2. I’m concerned – about you, your team, our ability to scale operations, etc.
    3. I’m willing to help in any way – if we can get to the root cause.
    4. I’m unwilling to continue with status quo
    5. I’m committed – Only reason I bring this up is because I care about you and I care about the company.  We need to find a solution. 
  5. Be clear about consequences.  I’m open to finding a creative solution quickly – Doesn’t need to affect your role or career here, but it’s getting to the point where it could. 
  6. Use silence as your friend.  It will give him time to think AND it will speak volumes without you having to say a word.

Ask questions:

Use positive questions to minimize defensiveness and maximize critical thinking.  Ask multiple questions before committing to a response – for example:

  • “Help me understand” / “What’s the situation as you see it?”
  • “What’s been harder than we thought?”
  • “What is the goal, as you see it?”
  • “What kind of help would you value?”
  • “What can we do right away to move toward the goal?”
  • “What would you do if you were in my shoes?”

Next steps: 

Plan in advance what your next action will be.  Invite them to share their own ideas on the next steps. Get a commitment from them on what they’ll do and what they can expect from you. Probably some form of…

  • “Take some time to absorb this conversation.”
  • “Let’s meet again on this in 1-week.”
  • “I’d like you to come back to me with a plan…”
  • “I want you to know we need to address this as a team… not the details, but that we’ve addressed it.”

All-star moves:

  1. Brevity.  Keep your comments short – and the meeting short. 
  2. Silence.  Don’t answer your own questions… let silence build constructive tension.
  3. Persistence.  Give them some time to reflect – allow them a second reaction.  But revisit the issue again and again until you see progress.
  4. Kindness.  Can you genuinely say you care, even love, the person you are challenging?
  5. Vulnerability.  Be honest.  I’m not very good at giving feedback; I should have been more clear.

Leadership Action: Give yourself 30-45 mins to prepare next time you have a hard conversation following these simple steps. You’ll be glad you did. Let me know how it goes?

Published by Keith Hadley

I am a Principal Consultant with Table Group... a card carrying leadership and strategy nerd and I sincerely believe that Organizational Health is the most powerful, enduring and ignored source of competitive advantage. My goal is to change the world of work by helping CEOs eliminate confusion and politics and in their ranks and to maximize productivity and morale — ultimately helping them accomplish their goals.

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