Reverse Mentoring

Diane Thielfoldt

Diane Thielfoldt is co-founder of The Learning Cafe (, a consulting firm dedicated to helping organizations develop, engage, and retain the talent of every generation. Also a workshop facilitator and an engaging speaker, she has educated hundreds of managers on issues involving the multigenerational workforce. She can be reached at

May 1, 2014

Mentoring is a powerful tool that can
work wonders in any
organization. It can become even more
powerful if you
“reverse” it and ask younger
employees to serve as mentors
to more seasoned workers—or even

What Is Reverse

Traditionally, a person with more
experience will mentor a colleague
with less experience. This method has
been proven through
master/apprentice relationships that
have allowed knowledge to be handed
down over hundreds of years. In reverse
mentoring, a more experienced
employee—ideally, a Manager or
Supervisor—actively seeks the
counsel of an employee with less overall
experience. This modern twist
has older employees turning to younger
staff for fresh perspectives,
trend spotting, and technology guidance.
As Alan Webber, Cofounder of
Fast Company, put it, “Reverse
mentoring is when the old fogies in
the organization realize that by the
time you’re in your forties
and fifties, you’re not in touch
with the future in the same way
as the young twenty-somethings. They
come with fresh eyes, open minds,
and instant links to the technology of
our future.”

Reverse mentoring refreshes learning for
veteran employees and Managers,
while helping to build the leadership
skills and experience of newer
employees—who are, of course, also
learning new insights from the
relationship. When you pair a Manager
with a Millennial employee
(someone born between 1977 and 1998),
the Millennial mentor gets a
glimpse into the world of leadership and
leaders—something that generation
particularly values, which is
one benefit of reverse mentoring.
Another is that it acknowledges that
everyone brings something to the
table—even those who have just
started their careers. Millennials have
skills, knowledge, and
experience that is valuable to tenured

Why Reverse Your
Mentoring? One Word:

Reverse mentoring has some unique
benefits that have to do with attracting
and retaining employees in the
Millennial generation—an essential
demographic for any
forward-thinking organization.
Millennials tend to prefer high-touch
relationships, have high exploratory
drives, and appreciate frequent
feedback. In other words, Millennials
and mentoring are a perfect match.

Here are 6 Millennial-specific
benefits to reverse mentoring,
which are just the tip of the iceberg:

1. Reverse
mentoring helps to retain and promote
younger talent. It creates a 2-way
conversation, allowing Supervisors to
learn what workplace conditions
younger employees seek in order to
advance themselves along with the
interests of the company.

Reverse mentoring engages younger
and newer employees, promoting their
loyalty and generating trust.

3. It empowers emerging and
established leaders.

4. Reverse
mentoring “shrinks” big
organizations by crossing boundaries
that employees would not normally cross.

5. It begins to close
the knowledge gap between long-time
employees and newer hires.

6. Reverse mentoring infuses an
organization’s leadership with
different, fresh, and younger

Who Else
Benefits? Everyone!

Reverse mentoring is
ideal in situations where you want
established employees and Managers to
gain technical expertise, whether
it is in business applications or
smartphone apps. The same is true of
learning about new and emerging trends
in marketing, or areas of work
and society that might impact your

It can also
strengthen the team even as it grows the
skills and strengths of the
individuals involved. For example, when
you pair a people-savvy
Associate with a Manager working on
winning over a prospective client,
everyone can benefit.

5 Ps of Successful Reverse

you send a seasoned Executive and an
Intern into a conference room and
say “go,” there are a few
high-level guidelines that you may
want to consider. No matter how simple
you intend the structure of your
mentoring program to be, take time to
make a plan. Follow these 5 Ps for
a successful implementation:

1. Purpose


3. Plan


5. Performance

Keep it Real

Many companies that implement
reverse mentoring programs have
straightforward objectives that range
from simply creating positive work
relationships between older and
younger workers, to more ambitious
outcomes such as transferring
technology savvy, new industry
expertise, trends, or cross- training.
The 3 most frequently cited reasons for
initiating mentoring programs
are retention, professional development,
and knowledge transfer.

Before you begin your program,
consider its purpose. That purpose
should be tailored to meet specific
(though perhaps broad) needs within
your organization. To determine those
needs, interview a mix of leaders
who are knowledgeable about your
organization’s challenges and
future. What needs do you hear?

Maintaining technical relevance

Keeping current with subject matter

Protecting and sharing
“tribal” knowledge

Connecting with consumer culture and

Growing future leaders

• Creating a
productive work climate

Keeping and growing talent

• Driving
multigenerational engagement

Your purpose is tied
to the results you wish to
see—your Mentoring Return on
Investment (MROI). You will need to
measure your MROI (see
#5—Performance), so set measurable
What kinds of actions or behaviors would
be evidence that the mentoring
program is working? Set out to seek
evidence versus proof, with
measurable results in areas such as:


• Professional

Transfer of scarce knowledge or skill

• Skill development

• Engagement

• Customer impact

• Succession planning

In addition to goals,
you should allow space for individual
innovation. List what the reverse
mentoring program is to achieve in
general, for all participants. Of
course, each partnership is unique, so
partners may also enjoy and
benefit from helping each other in ways
not defined by the program. A
young mentor might help a C-suite
Executive choose a new smartphone, or
a CEO might share tips on how a new
entrant can advance his or her
career. Factor in the need for informal
goals to be met as well.

Also consider whether you need the
support of your senior leadership
to help your program succeed. If so,
identify the key stakeholders and
describe what their involvement will
look like.

2. Partners:
Selecting and

a large extent, how you
determine who will participate, and how
you pair off participants,
depends on your specific goals and the
needs of the individuals and the
company. When pairing, consider that
personal chemistry is often
overrated. The best matches are often
mismatches, which broaden the
opportunities for growth in both
participants. Mentoring relationships
should not be restricted to people of
the same gender, or to those who
have similar backgrounds, because we can
learn so much more from people
who are different from ourselves.

As you match mentors to
partners, consider development and
learning goals, geography, diversity,
and (of course) generational
differences. Are your Managers willing
be mentored by a younger colleague?

People who are naturally
inclined to make the most of a reverse
mentoring opportunity have these

• Demonstrate positive job

• Build
effective relationships easily

• Continually develop job

Appreciate diverse ideas

• Are willing to try new

3. Plan the

To kick off your program, host a 2- to
4-hour orientation meeting with
all participants. This meeting should be
a comfortable, informal forum
for everyone to get grounded and
organized. The program’s
Coordinator can define reverse
mentoring, answer the whys about reverse
mentoring, and discuss the benefits.
Partners are introduced to each
other, and the pairs can begin to
discuss their own goals and

If possible, give
each pair some brief training
on learning and teaching styles, and
provide a general plan or guide for
the partnership. At a minimum, describe
a typical first meeting or
activity that partners can use to get
started (see “The First
Meeting” on page 24). As the
mentoring relationship progresses,
ask the following questions to each
partner to check the development of
the mentoring program:

1. Did your partner commit
to making this a relevant and productive
relationship—for example,
did your partner show a genuine
interest—and did you do the same?

2. Did your partner honor time
commitments—and did you?

Your kick-off
meeting should include tips
regarding generational differences. For
example: share insights into
generational differences; discuss
differences from perceptions to
attitudes among the various generations
in the workplace; and let
participants know how their generation
and others are perceived. At the
same time, caution everyone about
stereotypes and perpetuating stale
messages. Comments like “They
don’t want to pay their
dues” from tenured employees, and
“They’re stuck in
the past” from newer employees
will shut down reverse mentoring
efforts before they get off the ground.

Close the meeting by
outlining any logistics and details
involved in checking the progress of
the partnerships.

Progress: Prioritize and Persist

and tracking is crucial to ensure that
the program is effective. For the
first 2 months of a mentoring
initiative, the program’s
Coordinator or Sponsor should plan a
pulse-check every 2 to 3 weeks to
confirm that your guidelines and ground
rules are still in place.
Encourage partners to evaluate their
mentoring relationship.

After the first 2 months, scale back to
a monthly check. Ask for
participants’ feedback, focus on
catching any problems early, and
ask about successes. Remind each
participant that you are available for
support and troubleshooting.

How can you tell that the
mentoring relationship is working? Look
for the following success

• People are taking the time to
meet and work together

Partners are satisfied with the

• Partners are
benefiting from and enjoying the

Participants have ideas to improve the

shows that the biggest dangers
to successful mentoring relationship are
neglect (from lack of
commitment, time, and energy), breaches
of confidence, and the failure
to understand culture and generational
differences. As you implement
your reverse mentoring program, be on
the lookout for these pitfalls.
Asking partners questions about the
structure of the mentoring program
can help you calibrate and adjust:

• How
would you rate the time commitment? (Too
much, too little, just right?)

• To what degree did the
program provide the orientation,
tools, and ongoing support that you

Many participants report that the most
valuable part of a mentoring
partnership is the opportunity to learn
and stretch personally and
professionally. Publish, share, and
celebrate these successes! Check in
with partners and get their reactions to
the program with the following

What do you like best about the
mentoring program?

• What
do you like least about the
mentoring program?

• What
was your goal for
participating, and to what degree did
you accomplish your goal?

• How valuable has the mentoring
program been to your professional

5. Performance:
How Will We Know We Are

Part of your
plan should include evaluating the
success of your program, including
measuring and quantifying outcomes. The
Coordinator of the program
should perform all monitoring of
participating pairs, though he or she
may need some help with evaluation.

Your evaluation might
include questionnaires or surveys of
participants, individual
interviews, or observation of their
meetings. You are seeking to measure
some difficult-to-quantify outcomes,
including individual attitude and
behavior, as well as accomplishments.
Here are 4 ways you can gain
information to gauge success:

• Anecdotal
information related to the program goal

• Participant
survey (satisfaction/climate) results

• Feedback on

• Self-reported feedback from the mentors
and their partners

If evaluations indicate that
the program is not meeting its goals, be
prepared to make some changes,
re-train participants, or otherwise
support the program to ensure it is


Reverse mentoring can be a winning
situation for everyone involved. You can
cement the loyalty, interest,
and talents of your Millennial team
members; and more experienced
employees will realize that access to
new and different ideas can make
them more effective at serving clients
and driving earnings. In other
words, when you mix fresh, unbiased
perspectives with detailed knowledge
and strategic skills, the results are
innovation and increased employee
engagement across the board.


Reverse Mentoring

Sue, the Vice President of Human
Resources, asks Alan, a new 20-something
Sales Support Representative, to meet
with her monthly to share ideas on how
their company can create
opportunities that are exciting for
Millennials. In return, Alan gains a
rare inside view of how the organization

Rick is a young delivery driver who
lives and breathes social media. Once
his company’s Director of
Marketing discovers this interest, she
asks him
to add a regular meeting to his
schedule. He visits her office to
provide her with his personal feedback
and his generation’s perspective
on the
company’s social media

Mentoring Glue

To ensure that your reverse
mentoring program is effective, you need
to put some thought behind it. Take some
time to consider the “hard
and “soft glue” that can
hold a successful program together.

Hard Glue:

1. Clear boundaries and well-defined
expectations. Both partners need to be
clear on what they want to accomplish.

2. Agreed-upon rules. Each partner
must be fully committed to the mentoring
relationship, with

regular—at least
monthly—meetings and activities.
Partners should agree to be cooperative


Soft Glue:

1. Willingness to learn. In a
reverse mentoring relationship, both
parties must genuinely want to learn
from and share with the other.

2. Mutual trust. The goal is to push
each other outside of comfort zones and
try new ways of thinking, working, and
being. Ideally, the partners will
create a safe, professional, yet
risk-taking environment, and maintain

3. Transparency. Both partners must
be open with their feelings and with
what they are thinking. They must be
able to overcome differences in
style and be open to seeing
situations from different angles.

Your Launch Agenda

During the launch, provide guidance
and support for participants. Include
these topics:

• Why reverse mentoring, and
why now? (Make the business case).

• Set a level playing field.
(Use a tool such as an experience

• Set guidelines and personal

• Address differences in
learning styles.

“How Will We Know?

Quantitative Success Measures

• Number of people seeking

• Number of mentors who

• Number of people who have

• Number of development plans
that are implemented with mentor support
or influenced by mentors

• Employee or climate survey
results (questions related to career-
friendly climate)

• Number of meetings held with
mentors and their partners

• Number of personal and
professional goals achieved that are
attributed to mentor support

• Number of key employees
retained who have mentors versus
retention rates for those without

Qualitative Success Measures

• Self-reported feedback from
participants regarding the value of the
experience and the personal and business

• Feedback on increased
participant job effectiveness from
participants’ Managers

• Anecdotal information about
idea and best practice transfer across
departments, functions, or business

• Critical business projects
or initiatives that are positively
impacted because key participants
benefited from mentor involvement,
support, and/or
knowledge transfer

The First Meeting

The first meeting between the mentor
and his or her partner is like sitting
down to write a book and staring at a
blank piece of paper. How do you get
started? The answer in this case is
by getting to know each other.

The mentor—that is, the
younger employee—takes the role of
teacher. Regardless of who leads the
conversation or sets the agenda, it is
essential that both partners
remember the goal is for the Manager or
tenured employee to learn from a younger
counterpart and not take over the

mentor’s role.

The mentor can start the
conversation by telling stories and
encouraging his or her partner to tell
stories, giving specific examples
related to his or her
personal and professional
experiences. Both should share lessons
they have learned from
experience—whether on the job or
outside of work. This will
increase their credibility and
breathe real life into their

Here are some conversation starters
to kick off meaningful
discussions—conversations that

• What is something that most
people do not know about you?

• Discuss strategies to
balance work and personal life. What
have you learned that you could share?
What compromises have you made? How do
you feel
about them?

• Talk about your work and
life experiences. What have you done
that was unusual or controversial? What
experiences do you hope to have in the

• What mistakes have you made
that you thought would have a negative
impact on your career? How did you learn
from them? What would you do

• What is the smartest
decision you ever made, and why? What
did you learn that you would like to
apply to the future?

• What legacy are you creating
or building? What kinds of things are
you doing to pass along your expertise?

• What is some of the best
career advice you have received? Why?
How have you put it into practice?

What makes a conversation
comfortable and candid? The formula is
simple and the results can be
extraordinary. A great conversation just
takes curiosity and
a willingness to be changed or
stretched by another person’s