THE FIRST TIME MANAGER TOOLKIT

A guide for anyone who would like to coach individuals as they transition
into being a manager

Why coaching first-time managers is a powerful

way to develop them
Making the leap from being an individual contributor to a manager is a
difficult one. Ram Charan in his book “The Leadership Pipeline” describes it as
being the toughest of the six transitions in the journey of leadership.

The biggest challenge in this transition is that managers have to learn to let
others do work instead of doing it themselves. This means they have to learn to
plan, delegate, and learn to judge the performance of others. In terms of
values, the biggest change at this level is that they have to believe in the
usefulness of managers, instead of tolerating it.

Every first time manager faces different challenges and that’s where coaching
can play a vital role in their growth. Coaching allows stakeholders (whether
their manager; HR business partner or L&D partner) to help them create a
personalised plan for their success. Coaching can also help alleviate the sense
of pressure and isolation that first time managers often feel when they are
asked to take on tasks that they have never done before.
 The belief that they can think for themselves
and find solutions – it can be tempting to shift
into mentor/consultant role but staying with a
coaching approach can provide them the
support they need while also boosting their
confidence

The recognition that this is a difficult

transition to make – stakeholders may have
What mindsets do difficulty recalling how tough it was to first
you need in order give feedback to a former peer; how lonely it
felt to realise that you were no longer part of
to coach a first the peer group complaining about
management.
time manager?
The willingness to set aside the time to invest
in their development – these coaching
conversations are distinct from regular 1:1s
and operational meetings. It’s easy for these
meetings to be sacrificed at the altar of
deliverables so do make them sacrosanct for
both of you.

The ability to separate these developmental

conversations from performance
conversations – In order to build trust, do not
use this time to give them feedback and do
not use what they share here in other
performance discussions

Building trust and intimacy: communicating

that you are on their side and are there to
help them grow without any judgment of their What
struggles or ideas competencies do
Active listening: being empathetic; building
you need to be
on what they have said able to effectively
coach a first time
Creating awareness: asking questions that
help them think more deeply about the manager?
situation or their internal frame of reference

Action planning: helping them create

concrete action plans for themselves
What's a simple
process to follow
when coaching a
first time
manager?

Explain what coaching is

Tell them these conversations are safe spaces for them to talk about their
experiences of transitioning. Explain that your role in these conversations is to ask
them questions that help them process what is going on and in the process find
solutions that work for them.
Also, emphasise that these are not performance conversations and your goal is to be
supportive.

Set up a regular calendar to meet for coaching

Once a month for the first six months is a good cadence to have; you can adjust it
based on the intensity of their need.

Use the “Wheel of Transition” tool in the first meeting

This is a useful tool in the first conversation to help them identify the major pain points
they want to work through. From the second conversation onwards, you could use the
Wheel as a starting point and ask them which of the areas they want to work with.
The details of this tool follow.

Use the questioning tool kit in subsequent meetings

Ask them which area they want to work on and use the questions in the tool kit (that
follows later in this document) to work through the area they have chosen
Help them to make an action plan for themselves (using the action planning
questions)

Help them keep themselves accountable

Start the next meeting by checking in on the actions they had committed to (using the
review questions that follow)
Wheel of Transition
This is a simple tool to help first-time managers think about the various skills they need
to build and prioritise them. It can help the person you are coaching step back, take
an objective look at their situation, and in the process, be more mindful about the
actions they need to take.

To use it, show them the image below and explain: “The Wheel of Transition helps first
time managers prioritise their developmental efforts. The areas on the wheel are the
ones that most first time managers need to focus on as these are new skills. Please
take a look and see if you would like to replace any of these with other areas that
are more important to you".

(Once you have clarified that the areas are appropriate).

Take a moment to rate how happy you are with how you’re doing on each of these areas on a
scale of 1-10 (where 1 is not at all happy and 10 is very happy). Draw a line across each
segment based on the score you give it so the finished wheel could look something like this.”
Questioning Toolkit
Goal Setting
What challenges do you face with setting goals for your team members? Can you share
an example?
If you were to evaluate your goals against the SMART framework, what aspects are
working and what are not?
How do you feel when you need to have a goal-setting conversation?
In the conversations that you have had so far, what has worked? What hasn’t?
How do you explain the importance of a goal to a team member? What could you
strengthen about that?
What do you currently do to motivate the team member to take on a goal? How is that
working?
What kind of questions do you get from the team when they hear their goals? How do
you respond? What do you think is working or not working about that?
What do you think is going on with the team member you’re having trouble with setting
goals for? What can you do to incorporate that understanding in how you communicate
the goal?
.How do you feel when you have to set a stretch goal for a team member?
How have you felt given stretch goals in the past? What can you learn from that that you
can apply here today?

Delegation
(you may need to remind them of the difference between goal setting and delegation. Goal
setting is assigning a task to a team member that is theirs whereas delegation is when a
manager gives away a task that is theirs, in order to help a team member build skills)

What tasks do you find it easy to delegate? Which ones do you struggle with?
How do you decide which tasks to delegate?
How have you made choices about whom to delegate to? How has that worked so far?
What skills do you want individual team members to develop? How could you use
delegation as a way to build those?
What is one task you can delegate that you are holding back on?
What could hold you back from delegating as much as you would like to?
What factors would you consider when deciding which task to delegate and to whom?
What would you need to communicate when doing a delegation conversation?
What resistance do you anticipate you could encounter? How could you prepare for
those?
How would you like to measure the success of your delegation?
Time Management
(you could explain the urgent-important matrix - see
image)

What are the tasks that take up most of your time?

What kind of tasks do you struggle to make time for?
What percentage of your time do you estimate you are
spending in each of these areas? How do you feel about
that?
What could we do to reduce the time you spend on Q1
tasks? How are you currently managing these?
What are some tasks you can delegate to create more
time for yourself?
When in the day are you most productive? How are you
using that to plan your work?
What kind of distractions do you encounter most often?
What can you do to create some boundaries for yourself?
Describe a hypothetical day where you spent time well –
what would you be doing?
What do you need to let go off in order to make time?
What habits/thought patterns keep you from using time in
a manner that works for you (eg the thought that you have
to do everything perfectly etc)

Feedback
What kind of feedback have you had to give so far? What has been easy or difficult?
What challenges have you faced with giving feedback? How have you dealt with those so far?
How do you feel when preparing for a feedback conversation?
How do you prepare for a feedback conversation?
How do you normally structure a feedback conversation? What’s working about that and what’s
not?
Think of a difficult piece of feedback you need to give someone. How would you start that
conversation?
What kind of data do you use in a feedback conversation? Is there a way in which you could
make that stronger?
How do you involve your team member in thinking about the feedback?
What questions could you ask him/her to get them to take accountability for the change?
How would you close the conversation?
Assertiveness
What are situations where you find it easy to assertively communicate your point of view?
What situations do you struggle with? What makes these different?
What groups/stakeholders do you find it easier to hold your ground with? What works in those
scenarios?
What do you see as being the consequences for you/the situation when you are assertive?
Are there people around you who find it easy to be assertive? What do you see them doing
that you can learn from?
What goes on within you when you need to be assertive and are not able to?
How do you feel about having to say No?
What is the price you pay when you’re not able to push back or stand by your point of view?
Is there a situation coming up that you would like to be more assertive in? What is it? What
could you say there?
Would you like to practise a conversation where you need to be assertive?

Holding the team accountable

What do you think of when you hear the word accountable?
How do you feel about the fact that you now need to hold others accountable?
Can you think of a time when you were able to hold someone accountable? What helped you
do that?
What challenges do you have when you need to hold someone accountable?
What could you do at the time of assigning the task to communicate accountability?
What questions could you ask to check if the person has accepted accountability for the task
or not?
What are your normal ways of checking in while the task is underway?
How could you check if you are under-doing or overdoing those?
How would you bring up someone’s lack of accountability with them?
What could you do to support the person who is finding it difficult to hold themselves
accountable?
Building Relationships
How would you rate the relationships you have with various members of the team?
What words would you use to describe the kind of relationship you have?
What have you done to build those relationships?
What are some relationships that are not yet strong? What do you think is coming in the
way of building those?
Under what conditions do you build the strongest relationships? How could you create
those conditions for yourself?
How would you want your team to see you as a leader?
How easy is it to for you to acknowledge what your team members are doing well?
What do you do to encourage your team members to work together and build their
relationships with each other?

Stakeholder Management
Who do you see as being your most important stakeholders?
How strong are your relationships with those people?
What have you done to build relationships with your stakeholders? What’s working and
what’s not?
What are your stakeholders needs and concerns? What do you do to understand
those?
Who are the stakeholders you find easy to work with? What is it that makes those easy?
Which stakeholders do you struggle with? What makes those difficult?
What could you do to proactively offer support to your stakeholders?
What support do you need from them that you may not have asked for?
What would need to shift within you for you to work more closely with your
stakeholders?
What are some potential conflicts that you need to be prepared for?
Action planning questions
Help the first time manager make an actionable plan on whichever of these areas they
are working with using the questions below.

In talking about this today what has become clearer to you?

What did you learn about yourself?
What new behaviour would you like to experiment with before the next time we
meet?
What exactly would you like to do differently?
Where? With whom?
How would you like to measure the success of these new actions?
What support do you need to implement these?
What could come in the way? How could you overcome that?
Who could you ask for help in implementing these actions?
What would you like to hold yourself accountable for here?

Review questions
Use these questions at the beginning of the subsequent coaching conversation

How did you do on the plans you had made for yourself at the end of our last
conversation?
What worked well? What didn't?
What did you learn about yourself?
What came in the way of your implementing these plans (if that was the case)?
What would you like to do differently the next time?
For more information on this toolkit or on the first-time
manager programs we offer, please take a look at
www.navgati.in or write to [email protected]