FEATURE

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

By John Behr

E xtensive Gallup research1 indicates that millennials

in the workforce “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 stra-
tegic 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

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 Coaching Millennials For Leadership
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    approaches and support them when they act on their
Although many materials are available to help lead-
ers become better coaches, I’d like to highlight three
fundamental practices that deserve special notice—
and add two others that are rarely mentioned.  of the underlying tension coachees feel by setting an
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
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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 reac-
tion, 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
own initiative.
Develop trust by being open. You can relieve some
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.
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 Coaching Millennials For Leadership

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.  strengthened relationships—including not only
There is still a framework for 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.   of new hires and candidates for
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.  
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, you can 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
improved performance by your direct reports but
increased engagement shown by others down the line.  
Notes
1 https://www.gallup.com/workplace/238073/millennials-work-live.aspx
John Behr has coached executives
at numerous Fortune 500 companies
in the United States and companies
in Europe, India, China, Japan, and
Southeast Asia. He has completed over
3,000 full-scale executive assessments
promotion. His articles have appeared
in Harvard Business Review, Forbes, and
TLNT.com

Built-in Limits Would you like to comment?

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. 

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