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Step by Step mentoring

“We’re here for a reason. I believe a bit of the reason is to throw little torches out to lead people through the dark.” — Whoopi Goldberg

You have agreed to mentor someone, and now the first meeting is approaching. For me it was a nerve-wracking experience. What if you are found out not to be that impressive?. What if you give them the wrong advice? These are common feelings coming up to mentoring but soon fade as the real connection starts.


Today’s guide (Blog #95) is a short guide for new mentors or those mentors who wish to benefit from more structure to their interactions.

Step 1: Reflect and prepare to listen

Before diving into mentoring, understand your motivations. Why are you doing this? Reflect on your experiences, strengths, and areas where you can offer the most value. Reflect on the most vulnerable moments you have had throughout your career and how you might have benefitted from talking it through with someone you respect. These will all be valuable to draw upon for your future mentee.


Listen. You will be most valuable to this person, if you truly listen to what they have to say. You are not the expert in their life. This is a slower process than the “let’s solve it in this meeting” we are all used to. Listening and understanding first, helps you get inside the head of the person. This level of understanding gives you the information and rapport you will need to be able to work together on the problem-solving element of mentoring.


Step 2: The first conversation


You can help set the right tone in the first conversation and that will build dividends throughout the relationship. A calm and patient approach with an open mind is a good place to start. I have found that talking through my background and then my mentee's is a good place to start. That two-way sharing creates an atmosphere of trust as well as making your mentee feel that it is not all one-way traffic.

The first conversation is a great time to set expectations for each other. It is a good time to discuss how often to meet, and where and when the meeting might be. I tend to suggest every 4-6 weeks at the start of a mentoring relationship as you try and define the scope, and then every 8-12 weeks as the meetings transition to practical execution of your primary goal.

Step 3: Identifying the primary goal


An important thing to establish within the first one or two sessions, is “what is the primary goal?”. This is an overriding aim or objective that your mentee with your help can work towards.

Primary goals can be varied. Is it preparing for a promotion opportunity? or finding a new role externally? or even a 5-year plan to aim towards? A primary goal is rarely something that is teased out easily. Often the initial aims are more tactical like “handling my boss who hates me” (so common), or “How do I train for the next title up”. It is worth trying to talk this through with your mentee until you have something that gets to the root of it. 

In general most mentoring conversations will have mentees ask 4 types of needs:

  1. A need for a plan (where am I going?)

  2. A need to help navigate organisational politics (How do I get things done?)

  3. A need for recognition (why don't people appreciate me?)

  4. A need for change (How can I get outta here?)

Step 4: Keeping the conversation flowing

Not everyone, particularly those early in their career have mastered free-flowing conversation and this is made more difficult by not knowing someone well. You can help keep the conversation flowing.

This is mentoring not teaching, so a majority of the speaking should be done by the mentee. They hold all the information.

A good mentor should:

  1. Ask open ended questions, for example, what do you enjoy about work?)

  2. Respect quiet spaces. Often spaces is where people reflect or realise they have stumbled upon something of value. Often these spaces help connect ideas. Don't interrupt their flow.

  3. Seek clarity: Often mentees will say something that does not make sense or is incomplete. This is gold! Helping clarify unclear ideas is important as sometimes people overlook very relevant things.

  4. Summarise: When someone has been speaking for a couple of minutes, its important for them to hear their own thoughts reflected to them by a third party. Sometimes this mirroring helps clarify or even better helps spell out the magnitude of an opportunity or threat. To do this well requires paying attention, and leads to your mentee feeling their experience has been validated.

  5. Control reactions: If something said exposes injustice, danger, laziness or something else, do not react too much. You will influence people's train of thought if you interrupt them by providing strong signals of approval or disapproval. Better to reserve judgment until your open-ended questions help identify with clarity that something needs further scrutiny.

Step 5: Take notes

Written records of interactions are very useful. They don't need to be lengthy but record the key contours of what was discussed, some important facts about the person and agreed action points. This can be done afterwards or during.


Step 6: Accountability and action points

Over time the nature of the meetings change. Once you have developed a primary goal, action points are more important. Action points can include:

  1. Learning domain expertise: This might be reading an industry publication, a book, doing a course or finding someone to learn from.

  2. Networking: Getting to know others in your field who you can share ideas with

  3. Upskilling EQ: This includes i) communicating clearly and persuasively, ii) building relationships, iii) leadership behaviours, iv) emotional awareness, expression and control.

All of these skills are generically useful though. Later on once a primary goal has already been established, action points could be to develop habits in these areas.

Well defined and actionable action points in the form of "get a meeting with such and such to discuss your promotion criteria", "use clearer language in the upcoming pitch" or "grab coffee with one of your peers per day" are ones that can be tracked but even better if they have a specific measure of their success.

Obstacles to many action points are embarrassment or an avoidance of conflict on the side of the mentee. Sometimes it is addressing a behaviour by a colleague that is out of line, sometimes it is asking for additional responsibility or recognition. These obstacles are greatly lowered by role-playing the conversation. Once those words are spoken by the mentee they feel much less daunting.

After you have discussed general wellbeing, progress on action points should be second question at the next meetings.

Step 7: The challenging bits

Sometimes mentoring can get difficult. It can stray into territory that feels uncomfortable including:

  1. Asking for big favours

  2. Expectations of landing people a job

  3. Discussion of their very personal matters

  4. Asking questions about your personal matters

  5. Asking questions about your financial situation or compensation history

  6. Getting you to do a lot of work for them

I find a tactful 'I can understand why you want to know that, but that's not a direction we can go in' works well. The smoke and mirrors around compensation is concerning for junior employees. To the extent you know wide ranges or industry benchmarks it is not unreasonable to share it with them.

These moments will be rare and will be in general offset hugely by the pleasure of seeing someone grow.

So what?

You can give more from your mentoring if you

  1. Prepare and Listen: Reflect on your motivations and experiences before mentoring, and listen actively to understand the mentee's perspective. This establishes a foundation of trust and understanding.

  2. Set goals and engage: Identify a primary goal with the mentee by allowing them to reflect. This is achieved through open-ended questions and respectful pauses. Goals require action and make sure you take note of the agreed actions.

  3. Navigate Challenges: Handle difficult topics and uncomfortable questions with tact. Actionable advice and role-playing will help overcome career obstacles. Helping your mentee establish habits that upskill them and their EQ will pay long term dividends.

Thank you for joining. "Step-by-step mentoring" next week. Sign up to the subscription list on Blog | Deciders ( Follow me on twitter: @Decidersblog

Other blogs in the mentoring series:


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