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Help your team talk about topics that block success

Success depends on what gets talked about -- and what doesn't. This is the perfect space for the leader to step into. Here's how.

8 min read


Help your team talk about topics that block success

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As a leader, just thinking about what’s not getting talked about should scare the daylights out of you.

Creating an environment where everyone is comfortable speaking truth to power — and where it’s an expectation, not an exception to talk openly about tough topics — is one of the leader’s most important and difficult challenges. For most organizations and leaders, there’s a lot of work to do on this important issue. 

The right conversations are the difference between success and failure

Engaged in a significant strategic and organizational shift, one senior leader knew that success would only happen if her team could learn at hyperspeed. In her words: “Success demands we bring our individual, group and organizational failings to life quickly. We need to share ideas, no matter how radical, and we need to not pull punches on what we are doing wrong.”

I love this leader’s perspective. She understands, as all of us should, that the topics hiding behind the veil of collegiality or the smoke of organizational politics represent the opportunity. These unspoken conversations offer the potential for solving big problems, bringing new ideas to life and tuning our strategies to the realities of the market and our customers.

Simply stated: Success runs directly through tough conversations. If you and your team members aren’t having those conversations, it’s time for a change, and it starts with you as the leader. 

Beware the collegial management team

We had just signed the deal to sell our software firm to one of the largest business software providers on the planet. At a break during our initial meeting with the acquirer’s new CEO, I asked about his management team. His response spoke volumes: “They’re collegial, but they won’t face the big issues. As a result, I will have to change our culture on this team and probably change the members. We don’t have time not to tell each other the truth.” 

In a different moment that struck a nerve with me, our chairman, after observing our management team engaged in strategy work, offered: “The problem is you don’t trust each other enough to bring the real issues to light.” I recall rankling at this comment, only to process on it and realize he was right. It turns out trust is always an issue when groups fail to engage on the right issues. 

In thousands of hours of coaching and working with management and project teams, this inability to engage on the tough topics surfaces repeatedly. Interestingly, when you talk one-on-one with team members, they often share their frustrations, ideas and insights — all topics they’re uncomfortable raising in the group setting.

It’s refreshing to learn the team members don’t lack recognition of the issues or suffer from a shortage of ideas. It’s frustrating to know the answers are hidden below the surface of regular conversations, unlikely to be raised for various factors, including trust. 

It’s on you as team leader, senior manager, director, or executive, to fix this conversational constipation for challenging issues. Here are some ideas to help. 

6 steps to help open the tough conversation floodgates

1. Solve the problem for your area of influence

If you’re managing a team or function in an organization where messengers are regularly sacrificed and speaking truth to power might prove detrimental to your career, choose to change the rules in your area of influence. You can create an island of order in a sea of disorder. 

While you might not have the political heft to change the broader culture, you control the weather on your team or in your function. Make transparency a part of the group’s or team’s core values. Model the behavior always, and teach others to do the same. You might be shocked how positively people around you will respond to this island of openness.

And never discount the ability to drive culture change from the middle. While we assume all significant organizational accomplishments emanate from on high, the reality is quite the contrary. 

2. Embed openness on tough topics as an expectation, not an exception, in your organization’s values

The tone and tenor of acceptable conversations start with top leadership and the values they articulate and model in their daily encounters. If you’re a senior leader, it’s incumbent upon you to establish the need for conversations on the awkward, uncomfortable issues affecting the business as an expectation, not an exception. 

Too many of our organizational values are tired clichés that look good on the conference room wall but don’t regularly appear in our meetings or communication exchanges. The “expectation, not exception” verbiage, singles this out as table stakes for admission to the organization. It means tough conversations on topics that will make a difference are part of everyone’s day job and not something saved up for a someday that never comes. 

3. Practice swift trust

Our typical approach to giving trust — developing long-term, deep relationships — is deeply rooted in human history. After all, knowing who to trust in much of history directly impacted life or death. 

In today’s organizational settings characterized by temporary teams focused on specific initiatives, we don’t have time to take the slow path to decide if we trust each other. Instead, the practice of swift trust, where we make a leap of faith that someone who works with us is competent or wouldn’t be there, and then we backfill this initial impression with evidence over time, is a difference-maker in performance. Time-to-trust directly impacts time-to-performance. 

As an organizational or team leader, conversations on the tough topics will only take place if individuals perceive you value them and that you trust them. Any evidence to the contrary, no matter how slight, will shut down the flow of ideas and challenging topics. 

4. Thank the messengers

A crucial part of modeling the expectation for transparency on tough topics is how you respond to the messengers. While the message you are hearing might not be comfortable if it’s about you or something you did, the opportunity to listen, acknowledge and thank the individual for raising the topic is both critical and priceless. 

People and teams will take their cues from you on how they respond to feedback, critical observations or new ideas that challenge conventional thinking. In those moments when someone is courageous enough to raise an uncomfortable but important issue, you strengthen or weaken the communication culture by your response. Make the right choice and thank the messengers. And then do something with the insights. 

5. Embed these 3 questions in one-on-one and group discussions

I learned the 3W’s approach from a colleague years ago, and I share it far and wide. It’s three simple, easy-to-remember questions that help draw out the challenging topics when used consistently and authentically.

  • What’s working that we should do more of?
  • What’s not working that we need to change?
  • What do you need me to do to help you succeed?

You can start by shifting your one-on-one sessions with team members away from status reports to focus on those three questions. Use them with groups, your boss, your peers and your partners and customers. 

6. Ask for feedback on you until they believe you want it

The theme of you modeling the right behaviors is inherent in every technique in this article — none more important than people around you learning how important it is to get feedback on yourself. If this isn’t part of your leadership development approach, make it so. Chances are, your behaviors are a big part of what needs to improve for your team members and organization to succeed. Don’t be blind to seeing yourself as others do. 

The bottom line

The conversations you and your team members and peers are not having are the ones that should frighten you. Those unspoken conversations are opportunities foregone, ideas never brought to life and problems that will remain unsolved.

Given the state of our world and the challenges faced by every organization, the choice to open the floodgates and let the tough topics flow is truly a no-brainer. This good, hard work starts with you. 


Art Petty is an executive and emerging leader coach and a popular leadership and management author, speaker and workshop presenter. His experience guiding multiple software firms to positions of market leadership comes through in his books, articles, and live and online programs. Visit Petty’s Management Excellence blog and Leadership Caffeine articles.

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