Conversation ‘Crutches’ Make Difficult Discussions Easier

One of my close friends is a fitness trainer who often encounters difficult clients disagreeing with his professional judgment and demanding changes to their fitness regiment, nutrition plan, etc. He’s shared his frustration with me time after time as he tries to placate them and provide great “customer service” in the midst of delivering a difficult message (i.e., they need to lose weight to improve their health).

I gave him the same advice I give many managers and leaders: Develop a handful of “conversation crutches” you can sprinkle in here and there to make the difficult conversation a lot easier (and quicker in many cases).

If you polled 100 managers asking what they dreaded most in their leadership role, I’m sure many would say they’d prefer a trip to the oral surgeon to having a difficult discussion with an employee. No one wants to tell an employee he or she is not meeting expectations in one area or another.

We all know that no one is perfect—everyone has weaknesses (which we prefer to call developmental areas )—but the thought of having to provide that constructive criticism or provide feedback that may cause conflict is gut wrenching nonetheless. To make matters worse, we realize that as managers, it’s a large part of our job (if we’re doing our job) to help others identify and improve areas of weakness.

Deep down we know that the best bosses are not the ones who tell us we’re so wonderful that they can’t think of anything to improve but the ones who highlight areas for improvement and motivate us to become even better.

Delivering constructive criticism may never feel good, but it’s certainly a critical element along the path of employee development. Unfortunately, many managers make one of two common mistakes. They often either…

1) Avoid the conversations altogether and thereby rob the employees of the opportunity to improve.

2) Provide such vague/sugar-coated feedback that the constructive message is lost and/or misinterpreted (e.g., Jeff who’s chronically late to team events leaves the meeting with his boss thinking that his chronic tardiness is really an asset as it shows his dedication to juggling so many events and demands at once!).

So the question is: How can you deliver the message in such a way that gets the point across while preserving the relationship?

While there’s no foolproof easy answer, a key for me has been developing “conversation crutches”—easy-to-remember phrases/vignettes you can sprinkle into conversations as needed to help deliver a difficult message with candor, tact, and sensitivity.

Approach #1: Ask employees to evaluate the situation or identify the issue/development area first.

This is a powerful technique because it not only typically softens the feedback you need to give but it also provides a deeper coaching opportunity because it provides insight into an employee’s perspective. This insight can further inform your subsequent feedback for them as appropriate:

“I’ve usually found that if I’m open to it, I can learn more from ‘failures’ than ‘successes,’ so I encourage you to not shy away from identifying improvement areas. I think this position is a great fit for you in part because there is a bit of a learning curve so you’ll learn a lot if you’re open. As part of that process, you’ll likely have a few mishaps early on. Let’s expect those and take some time periodically to check in and analyze areas where you’re excelling and areas where you might need a bit more training and coaching over the next few months. How does that sound?”

“Jill, what a long meeting yesterday. If you don’t mind, I’d like to take a few minutes to debrief it—discuss what worked well and what we might have done differently. Is that OK? Why don’t you go first? What do you think worked well? Now, what do you think you might do differently next time? Can I offer my thoughts?”

“If you had to pick your top two strengths and weaknesses, what would they be?”

“Jill, of course we all have weaknesses and I know your standards are so high that I’d like to share an observation with you from the meeting yesterday if I might. Are you open to that?”

Approach #2: Emphasize that your responsibility as their manager is to point out areas of weakness. Indeed, you’re helping them by raising difficult issues.

Example: “I feel that a perception is being created, and I want to make you aware of it as soon as possible so we can decide how to best move forward. You’ve been out of the office quite a lot this month due to training, vacation, and telecommuting, and I think it’s creating a perception that you’re not as available as others on the team. I want to be sure we correct that perception as soon as possible because I know that isn’t your intent. What are your thoughts?”

Example: “I feel like a large part of my responsibility as a manager is to alert you anytime I see an area for potential improvement so you have every opportunity to address it before it becomes an issue. Also, I don’t believe in surprises during appraisals or formal evaluations. I remember as a team member early in my career feeling it was unfair for my boss to bring up issues during formal evaluations that hadn’t been previously brought to my attention, so I vowed not to do that when I became a manager.”

(I don’t suggest saying anything that isn’t true. In my case, this was my experience early in my career and I found that sharing it was helpful context for me to share difficult information with team members. Some fully agreed and made a point of thanking me for raising the issue to them early so it didn’t necessarily affect their evaluation at the end of the year.)

Approach #3: Part of the difficulty with delivering constructive criticism is that it can be hard to do it without the employee feeling attacked and becoming defensive. As a result, it’s important to remember crutch phrases that minimize this potential impact.

Instead of saying “No” to a request, consider saying, “What would work better for me is….”
Remember that people often feel attacked when “you” language is used. For particularly sensitive discussions, try to use “I” language, which minimizes the likelihood of feeling attacked. (Don’t try to do this all the time, though, as it may dilute your message too much if overused).

Example: “Jill, I’m somewhat concerned about our cycle time producing the marketing report. I understand it’s been late the last two months. What are your thoughts about that? What could we possibly do to ensure the report is delivered on time moving forward?”

Everyone responds defensively to labels whether the label is accurate or not. So, avoid labels at all costs and instead cite behavior/objective facts. Also, remember that as soon as you label someone, they’re going to ask for an example immediately anyway, so just skip to the example.

Don’t say: “Jill, you seem a little antisocial and I’m concerned about that since it’s so important to build a strong relationship with this client.” Instead, reword it this way: “Jill, I noticed last week that you didn’t eat lunch with the client team during the kickoff meeting or attend the social Friday night. It’s so important that we build strong relationships with their team so that concerned me a bit. Your thoughts? What can we do moving forward to ensure we’re building strong relationships with them?”

To enhance the effectiveness of these interventions/discussions in general, it can help immensely if you establish ground rules/practices early on before there’s a need for a difficult discussion. Some of these practices might include agreeing to debriefing meetings afterward to consider what worked and what didn’t, conducting standard feedback sessions every 90 or 120 days, or agreeing to ask permission to raise a “hard issue” when necessary.

Although these crutches can be helpful, don’t misconstrue them as a blanket recommendation to soften all constructive criticism or difficult messaging. Sometimes, softening the message can be the wrong move, so you should be as direct as your personal comfort level and the maturity of the relationship will allow.

Often, it’s appropriate (and necessary) to be firm, direct, and to the point. However, if you have situations where you run the risk of avoiding the conversation/issue because you just don’t know how to deliver the message, consider using these “crutches” to help you say what needs to be said.

Dana Brownlee is a keynote speaker, corporate trainer, and teambuilding consultant. She is president of Professionalism Matters, Inc., a boutique professional development corporate training firm.


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