An unexpected payoff

Sometimes you learn you are not as funny as you think.  Years ago as a rookie plant supervisor, I had the simple task of handing out paychecks every two weeks. (This was pre-direct deposit.) On that first payday, I decided to spice up the ritual of going from workstation to workstation passing out pay envelopes. As I met each employee, I would say such things as:

“Hey, Rick, here’s your paycheck. Did you work hard for it this week?”

“Jane, big money in this envelope for you. Try not to spend it all at once.”

I thought I would win the award as the funniest supervisor around. Instead, when I finished my rounds, I found Jim—my senior technical lead—at my little supervisor’s desk.

“Sit down,” Jim began with a half-smile. 

“You know, the buzz is that you’ll do OK as the new boss.” Jim said, “But I’ve got to tell you right now, when you pass out paychecks, shut up.”

I was shocked and embarrassed, as I thought everyone would appreciate my paycheck comedy. Jim’s sit-down with me exposed a blind spot that would have annoyed my employees every two weeks. Jim became my first truth-teller and trusted advisor. I checked in with Jim regularly to hear how I was doing. And if I forgot to ask, I would find Jim at my desk, letting me know when I needed to get back on track with the team. 

Thanks to Jim, I’ve always sought a trusted advisor in every job, especially in new organizations and tough roles. At every stage of my work and teaching career, I’ve found myself listening intently to a truth-teller, spelling out how I came across to others, and offering ways to improve. My trusted advisors keep me in my learning zone. They boost my confidence to hear the message and prompt my humility to remind me that I am still on the leadership journey. 

Breaking the boss booster-bubble

Truth-tellers  (let’s call them T2 for short) can help you overcome blind-spots and traps that often snare us as we advance in a career. Tonya, a high-potential talent in one of my Executive MBA classes, affirmed the value of listening to others. “I get plenty of feedback about me and, candidly, it’s quite positive,” she said. Knowing her abilities, I agreed that there was merit in what she was hearing. But I asked her whether most leaders hear the whole story of their actions.

The boss has more power and status so those around them become cautious. People start filtering comments. “Do you think people are anxious to please their boss with just the good news?” I asked. Savvy leaders know to probe for more and avoid being seduced in a bubble of booster flattery. As one newly appointed manager told his team in the first staff meeting, “I don’t want to hear only the good news; I want to hear the whole story—good and bad.”

How to find your next truth-teller

If you want to hear the whole story, you’ll need to cultivate a valued set of T2s.  But how do you find one? Start by looking around in six ways:

Look Down:

Is there someone on your team who could offer observations and insights on how you are coming across to your employees? As with all potential T2s, you’ll need a solid level of trust, mutual respect and the right chemistry. These T2s are usually more senior employees on your team who can offer feedback based on their work experience, team connections, and organizational savvy.

As the first step in your next one-on-one meeting, tell your T2 employee you are interested in being the best leader possible and are curious to learn what’s working well and what’s something you could do better. You could ask how your leadership has been impacting the team lately and what’s something you should be considering (or missing) that would improve things. It might take a few conversations to get the real scoop and be sure to demonstrate attentive listening and openness to what you hear.

Look Across:

 Is there a peer or colleague who could offer T2 peer coaching? Peers can provide a rich source of feedback and wisdom, often seeing a fresh perspective or organizational reality you might miss. A coffee chat with a T2 peer unlocked a productivity dilemma Samantha faced. As a new leader for a large retailer, she was frustrated and exhausted from trying to turn around a low-performing unit. “Until that conversation, I didn’t realize the importance of relationship building with my colleagues and seeking their input before initiating changes that impacted them,” she commented. “That conversation opened my eyes to how I was being seen and the importance of slowing down and taking the time to reach out to my peers for help.” Samantha found her peer T2 didn’t have a personal agenda, was motivated to help her and had the best interests of the organization in mind.

Look Up:

Is there a potential T2 for you at a higher level in the organization? While usually not in the direct chain of command above you, consider a T2 conversation with a peer of your manager. As with trusted peers, a view from above can provide valuable guidance and a more strategic perspective on what’s going on. I benefited from such a T2 resource early in my tenure as the head of talent development in my last corporate role.

My new job meant I was often on the agenda at CEO staff meetings. In my first few meetings, I struggled to make clear points or respond concisely to questions. Fortunately, I had hit it off with the senior sales executive who attended these meetings. I reached out for his feedback on how I was doing and how to improve. Throughout the next few sessions, he provided candid tips that helped me find my authentic voice and executive style with the senior team. And while my manager was also helpful, I found the observations from another executive to be priceless. One caution to pass along: tread carefully when establishing a higher-level T2 connection, so it’s not seen as a threat to your direct manager. 

Look Back:

Still not sure where to look for help? Another place to find a T2 is by looking at your calendar. Look back at the last 30 days and preview the next month of meetings. Who we spend time with is a rich source of potential T2 advisors. Joshua, a regional sales manager, found a T2 after reviewing his recent appointments. Much of his time is spent with external stakeholders, and he reached out to an outside partner he trusts and sees in action frequently. 

Look Diverse:

 Aim to expand your potential T2 sources.   Research reminds us that we tend to limit our feedback-seeking efforts to those like us and may narrow down what we can learn. While similarities make the T2 conversations more comfortable, they may create another set of blind spots and miss the richness of insights from a broad spectrum. Reverse mentoring is an example of reaching across the generations for advice. Even if you have a few T2 people in your network, look to see if adding someone new will leverage diverse perspectives, backgrounds, and talents.  

Look Coachable:

In addition to seeking out a T2 relationship, act in such a way to help truth-tellers find you. Personal brands and reputations are part of the work environment; make sure you signal openness and curiosity as part of your brand. Be sure to respond well when a T2 offers you feedback. Be ready when someone pulls you aside and says, “Hey, do you have a minute? I’d like to share something.”  Suspend judgment at the moment, listen to understand, and end with a “Thank You. I know giving feedback can be hard, and I appreciate your help. Let me consider what I’ve heard.”

Throughout my career, I’ve benefited from T2 coaching. Jim helped me cut out my comedy act and show respect for my team on payday. That Sales Executive pointed out how to sit at the table well with the CEO staff. Sometimes the feedback was affirming, and sometimes it was hard to hear but it always helped me be better. Consider how you can establish or expand your network of truth-tellers. The good news is they are all around; you just have to look and ask. 

Note: Part of this article was adapted from Coachability:  The Leadership Superpower, Kevin D. Wilde, 2022, Pond Press Reads