Coaching, executive coaching, global Leadership, reinforcement in executive coaching

Coaching Millennials for Leadership: What they need to learn and how bosses can coach them effectively

(This article was first published on February 4, 2020 in the Leadership Excellence magazine)

Extensive Gallup research1 indicates that millennials in the work force “want coaches, not managers.”

And bosses can be effective coaches. They have two advantages over external coaches in that they know their direct reports better and they can come up with assignments tailored to individuals to help them develop leadership skills. The main disadvantage is, of course, that the coach is the boss, so there will be limits to the candor shown by their coachees.

What do younger leaders need to learn?

Largely millennials require the same leadership skills most leaders need, ranging from delegation and strategic thinking to decision-making and aligning their teams.

One development area I sometimes come across that’s specific to younger leaders—not just millennials—is an unwillingness to compromise, e.g., to meet people halfway, accept something less than good in order to get another good thing done, be nuanced in communicating, and recognize that there isn’t currently enough support in the organization for a major and apparently much-needed change.

Many millennials and other younger leaders see compromising or “being political” as losing their integrity. They need to discover that we can compromise in useful ways, and do so without losing our integrity. This is a critical lesson for those who aspire to leadership as opposed to those who want to be individual contributors.

But younger leaders do need to be vigilant. What starts out as a realistic compromise or two can end up being a chronic departure from one’s fundamental values.

Nevertheless, the paradox holds: you can compromise without losing your moral compass.

Another mindset I often come across in younger leaders is a reluctance to promote their own strengths and potential. To many, it just seems wrong. I counsel them that they’re doing the organization a favor by letting colleagues and superiors know what they’re good at so that optimal use can be made of their talents. And I find that, even when they acknowledge the truth of what I’ve said, some still need on-going encouragement and concrete suggestions for steps they can take.

How bosses can be more effective coaches  

Although many materials are available to help leaders become better coaches, I’d like to highlight three fundamental practices that deserve special notice—and add two others that are rarely mentioned.

As a coach, you need to:

Become an effective listener.

There are a number of commonly cited best listening practices, but it’s worth singling out the ability to be patient and to withhold judgment.

Being non-judgmental while listening definitely requires patience, and it takes practice to learn because we judge reflexively when hearing others talk and we usually have a pre-existing“take” on the other person that’s hard to separate from what they’re saying at the moment.

Assume the positive

This is part of effective listening and withholding judgment, but it goes further. Often we tend to assume the other person is defending, justifying, or self-promoting, and this frames our reaction, whether we express it verbally or otherwise.

But you can change the whole tenor of an interaction if you start by assuming the other’s intentions are positive and constructive. This doesn’t mean you have to live on an imaginary cloud, divorced from reality. But it does mean recognizing that anything you say, even criticism, which issues from an over-arching positive frame of mind on your part will be more easily received.

Ask open-ended questions

Instead of questions that prompt yes or no answers (like, “Do you like your job?), learn to ask open ended questions (“What do you like most about your job?”). Or:

Is there any way we could be helping you do your job better?

What would you like to see happen that isn’t happening now?

These questions are not only less risky for coachees to answer but yield responses more likely to help you understand them. Questions like these also signal your willingness to recognize coachees’ individual approaches and support them when they act on their own initiative.

Develop trust by being open

You can relieve some of the underlying tension coachees feel by setting an example of openness and vulnerability.

By trusting that your openness will be well received, you gain trust from coachees.

You might say something about the nature of your interactions with the other person, your own work situation, other colleagues, your own limitations or personal concerns.

For example:

“Ï’m wondering if we’re fully understanding each other. Do you think so?”

“I have a really hard time with Tom.”

“Do you think I talk too much at meetings? I thought I went on and on this morning.”

This is a particularly good approach to use with millennials because studies show they want to work for leaders who regularly seek feedback on their own performance.

Trust the process and let it unfold

Many coaches have found that they sometimes strike gold when they listen without an agenda. The paradox is that, from time to time, the best way to get where you want to go in a coaching session is to, temporarily, stop trying to get there.

There is still a framework to the conversation, so the two participants are not simply wandering about. But when the discussion is allowed to take its course, it often ends up going in directions that yield significant insights for both of you. It’s similar to the dynamic involved in brainstorming sessions, where ideas are allowed to develop free from immediate criticism.

Of course, time is limited for both you and your direct report. Knowing when to carefully guide the discussion or let it flow is a sensitivity developed over time. It doesn’t always bear fruit, but the fact that it sometimes pays major dividends makes it worth trying.

Letting things unfold may also allow you to relax more, and this is communicated to coachees, making it easier for them to open up and respond constructively.

Built-in limits

Even though you make it clear that you’re wearing your development rather than supervisory hat for these coaching sessions, there’s still no getting around the fact that you’re also the boss.

Your direct reports may consider it too risky to say what they really think about your initiatives or about coworkers, other executives, job conditions, and company policies. And they may avoid mentioning any outside-the-workplace circumstances impacting their performance.

The good news is that a lot can still be accomplished without having to hurdle these obstacles. There are so many areas you can talk about without getting into risky issues. And, over time, as coachees develop trust in you, some of those obstacles will fall away.

It can also happen that, for reasons of temperament or working styles, you and one of your direct reports simply aren’t a good match or that discussions end up continually going over the same ground. When this happens, youcan look for a colleague or someone from another department entirely or an external coach to provide the help younger leaders are looking for.

Note also that, even if no specific capabilities have developed from your regular coaching sessions, substantial benefits may ensue as a result of strengthened relationships—including not only improved performance by your direct reports but increased engagement shown by others down the line.