How To Safely Navigate A Critical Conversation

Sooner or later, it’s going to happen.

Faced with having a conversation you’d rather not have; you’ll hear the clock ticking in the background and recognize the urgency of the moment. Still, a part of you wishes it would all just go away, that if a pair of red shoes worked for Dorothy, they might work for you as well.

Then reality hits, and you resign yourself to the fact that it’s “Go” time.

Proactively considering the intention, impression, and impact of the ensuing exchange will not only help navigate dialogue but can work to strengthen an existing relationship in the process.

While this describes a classic approach to communication, we’ll stay closer to circumstances that mark a point of transition, conversations leaders will inevitably encounter along the path toward a better tomorrow.

You Never Forget Your First

My first critical conversation as a young Coast Guard officer involved an Annual Performance Review for Petty Officer Reed. I was a little over six months removed from the Academy but had observed enough to know this 15-year veteran was in way over his head.

It wasn’t his fault. With a knack for being the most convenient option in the right place, at the right time, he had ascended the ranks without the proper guidance or development. His technical skills were far below average, and his people skills weren’t much better.

I was tasked with communicating to Petty Officer Reed that the professional life he had grown comfortable living was about to change.

My misguided intent was to draw attention to his shortcomings, to impress upon him the urgency of his situation. I didn’t think about the impact of my approach beyond generating a basic awareness of how far behind his peers he was.

It didn’t take long for the nightmare to begin.

I made the critical error of first handing him a copy of his marks to review, without framing our conversation or providing any constructive dialogue. As he reviewed the cascade of negativity, he began to refer to himself in the third person:

“These are not marks for Petty Officer Reed. There is no way Petty Officer Reed deserves this.”

My tongue began to swell as I grasped for examples relevant to the assigned marks. Just my luck . . . that part of my brain was out to lunch. I couldn’t remember the specifics used to correlate the evaluation.

While Petty Officer Reed never crossed the official line of disrespect, my failure to provide accurate and practical reasoning earned a not-so-veiled reference in the on-going third person conversation:

“Petty Officer Reed shouldn’t stand for this treatment from some snot-nosed kid.”

You think it only happens in the movies, then you hear yourself referred to as a snot-nosed kid.

My stateroom went silent. We both sat there staring at each other.

In that moment I could sense the hurt and disappointment in his eyes. Petty Officer Reed’s career was based on shadows, but he was right about one thing . . . he didn’t deserve to be notified of that in this manner.

While we somehow managed to work out a basic plan by the end of that meeting, I knew it was an experience that I never wanted to repeat.

A Proactively Pragmatic Approach

That would launch a career filled with critical conversations, each one respected for its unique purpose and energies invested.

It’s not to say these opportunities become easier over time or with experience.

Like stage fright or performance jitters, a healthy dose of apprehension and uncertainty means you’re approaching potential dialogue with due diligence and the respect it deserves.

You will become more adept at understanding what’s at stake: This is someone who has trusted you with guiding their growth and development. You owe it to them, and to yourself, to communicate necessary changes with complete transparency.

Some conversations will play out differently than expected. That’s why building proficiency in this pragmatic approach has incredible value. Repetition will create cognitive memory, driving these behaviors deep into your subconscious where we want them to be.

That way your conversations won’t sound scripted or rehearsed. Because you’re beginning with an end in mind, a sense of empathic empowerment will guide dialogue to mutually benefit all parties involved.


Why do you need to have this conversation?

Chances are, something needs to change. Determine your participant’s current state regarding:

  • knowledge necessary to perform routine tasks (enable)
  • emotional connection to a task (empower)
  • desire to exceed the expected (engage)

These act as navigational beacons for your mindset, helping you remain focused on the behaviors involved, not the individual. Remember . . . just because someone’s performance has fallen short of expectations, it doesn’t make them a bad person.

You don’t want to appear void of emotion, but your intentions should support growth, discovering ways to overcome obstacles through awareness, insight, and at times, corrective action.

This will also build confidence necessary to pull through your intention and not be distracted by the participant’s attitude, emotional state, body language, reference to you as a snot-nosed-kid, etc.


What type of impression do you want to generate from your conversation?

Based on a feeling or opinion without conscious thought, creating the right impression to support your intended outcome adds merit in the eyes of your participant. This includes being prepared with examples or background information during your dialogue.

In my performance review with Petty Officer Reed, I gave the impression of being mis-informed, unorganized, and judgmental when I couldn’t provide specific examples that justified the marks assigned.

That adds fuel to the fire and damages the health of your relationship moving forward.

Be creative in the location and setting of your conversation. If we’re talking about knowledge necessary to do the job, maybe your office is the most appropriate setting.

If empowerment or engagement is the focus, perhaps a neutral location is best, one that encourages an open and insightful exchange. Either way, choose a setting in which you feel comfortable exploring potential changes.

Your participant will feed off your authentic intentions, enhancing their perspective of the conversation and willingness to share.


What will be the extended influence of this conversation?

While your intention and impression relate to maintaining a proper mindset and promoting a growth-related dialogue, impact is straightforward current state vs. future state.

Identifying and then maintaining sight with your destination is the ultimate value of a critical conversation.

Think of it . . . have you ever walked out of a conversation that felt good, went better than expected, then realized nothing was agreed to or accomplished?

Remember that you engaged in this conversation because something needed to change. Write it down if that helps, but something must trigger an alarm if you’re in danger of not reaching your overall objective.

Soliciting Input

When I listen to someone lamenting, “Ugh, I’m so not looking forward to having this conversation,” what I hear is a person not prepared for the opportunity at hand.

If you have sensed the need for change, or observed questionable behavior or performance, having a critical conversation becomes a necessity. This applies both to the environment you supervise, and the relationship you share with your leader.  

Set your intention by identifying why the conversation needs to happen. Choose an environment or setting that subconsciously implies a supportive impression. Then generate the impact of extended influence by communicating your future state objective.

Engage your participant in dialogue and solicit input as appropriate. This spirit of collaboration will go a long way to sustaining behavioral and performance adjustments, which is after all, the ultimate value of a critical conversation.

Thank you for spending your Tuesday with Tall Tim Talks!    

Leave a Reply

Fill in your details below or click an icon to log in: Logo

You are commenting using your account. Log Out /  Change )

Facebook photo

You are commenting using your Facebook account. Log Out /  Change )

Connecting to %s