Three Practical Mentoring Tips That Actually Work

How to make mentoring easier.

Mentoring sounds very serious sometimes.

People picture two professionals sitting in expensive chairs, saying deep things like:

“Tell me about your five-year vision.”

Meanwhile, real mentoring is usually more like:

“I have no idea what I’m doing.”

“Yep, been there.”

And honestly? That’s why mentoring works.

Good mentoring is not about pretending to have a perfect life. It’s about helping another person think clearly, solve problems, and move forward without losing their mind.

I’ve been mentoring for years now, and over time I’ve noticed something important:

The best mentoring is practical.

Not motivational poster practical.

Actually useful, practical.

The kind where, after a conversation, someone thinks:

“Right. I can actually do that.”

So here are three practical mentoring tips that have genuinely helped me over the years. They’re simple. They’re easy to apply. And most importantly, they work in real life — not just in leadership books written by someone who apparently wakes up at 4 a.m. to meditate on productivity.

Have a Process, or You’ll End Up Having the Same Conversation Forever

One of the biggest mistakes in mentoring is having no structure.

Without structure, mentoring can slowly turn into two people meeting repeatedly to discuss the exact same problem in slightly different ways.

You know the kind of conversation:

“So how’s that thing going?”

“Still bad.”

“Right. Same time next month?”

That’s not mentoring. That’s a sequel nobody asked for.

This is why I use a workbook process in my mentoring. The workbook is a simple, structured document—nothing fancy or overwhelming—that guides our sessions with prompts, goal-setting exercises, and space for reflection. Each section helps track progress, capture key insights, and break down big goals into smaller, manageable steps. Having this tool on hand means both mentor and mentee can see where they started, what they've accomplished, and what comes next.

A workbook creates a beginning, middle, and end to the mentoring journey. It gives the relationship structure. It creates goals. It tracks progress. It helps both people know where they are going.

And honestly, people need structure more than they think.

Because motivation comes and goes.

Life gets busy.

People forget things.

And after three months, most of us can barely remember what we had for lunch last Tuesday, never mind the brilliant action plan we created during a mentoring session in February.

Having a workbook or mentoring framework helps keep things moving forward.

It also removes pressure from the mentor.

Many mentors think they need to arrive at every session carrying magical wisdom from the mountain.

You don’t.

You just need a process.

The process does a lot of the heavy lifting.

A good mentoring structure helps people:

• Set goals

• Reflect honestly

• Track progress

• Build accountability

• Stay focused

The other thing structure does is create momentum.

Small progress matters.

Very few people transform their lives because of one amazing sentence from a mentor.

Most growth happens through repeated small conversations over time.

That’s why having a process matters.

It helps mentoring become something more than “a nice chat.”

If you want support building a mentoring process, that’s exactly why I created my workbook resources at Project Skills Mentor.

Because mentoring works better when both people know where they are going.

2. Always Have a Pen and Paper Nearby

This sounds incredibly simple.

Because it is.

But honestly, having a pen and paper during mentoring conversations has probably saved me hundreds of times.

Most of my mentoring now happens online. And online conversations can get messy fast.

People share ideas.

Goals change.

Stories overlap.

Someone mentions a challenge today that connects to something they said six months ago.

If you don’t take notes, your brain eventually starts buffering like a bad Wi-Fi connection.

So I always keep notes during mentoring conversations.

You don’t need to overthink it. Just start by grabbing a notebook or opening a blank document and writing down a few basic prompts you’d like to ask in your sessions. You can jot some questions about goals, challenges, and next steps, or look up a free template online. The key is to have something tangible to help organize your conversations and keep track of progress as you go.

Just enough to follow what I call the “red thread” of the conversation over time.

That red thread matters.

Because mentoring is not one conversation.

It’s a long conversation spread across months or even years.

And when I start a session by saying:

“Last time you mentioned struggling with confidence during presentations. How did that go?”

…people immediately know I was listening.

That matters more than people realize.

Good mentoring is not about delivering speeches.

It’s about paying attention.

I also write down:

• Actions we discussed

• Resources I want to send

• Ideas they want to try

• Problems they’re working through

• Things to follow up on later

Next time we talk, we can continue rather than restart from zero.

And here’s the funny part:

Half the time, people already know the answer to their own problem.

They just need someone to help organize the chaos in their head long enough to see it clearly.

That’s why note-taking helps.

It helps you spot patterns.

You start noticing:

• recurring goals,

• recurring strengths,

• recurring excuses,

• and recurring moments where someone is far more capable than they realize.

Also, practical point here:

Write things down when you promise to send something.

Because nothing destroys mentor credibility faster than:

“I had a great resource for you… somewhere… in my brain… possibly.”

Your future self will thank you for taking notes.

Your mentee will too.

3. Listen More Than You Talk

This is the big one.

And honestly, most mentors are worse at this than they think. Almost everyone struggles with listening at first. It’s normal to find yourself wanting to jump in or worrying that you’re not being helpful enough. If that’s you, you’re not doing it wrong—you’re learning. Being a great listener takes time and practice, and making mistakes is part of getting better.

A lot of people hear the word “mentor” and immediately think their job is to become a motivational podcaster.

So they start giving advice immediately.

But mentoring is communication.

And communication is a two-way street.

Sometimes people don’t need advice yet.

Sometimes they just need space to process their thoughts.

Talking helps people think.

That means your first job is usually not to speak.

It’s to listen long enough to understand what is actually happening.

Before jumping into advice, ask one or two clarifying questions first.

Not twenty-one questions.

This is mentoring, not an airport security interview.

Simple questions work best:

• “What part of this feels hardest?”

• “What outcome are you hoping for?”

• “What do you think is getting in the way?”

That’s usually enough.

Then ask something really important:

“Would you like advice on this, or would you rather talk it through first?”

That question changes everything.

Because sometimes people already know what they want to do.

They don’t need a brand-new answer from you.

They just want reassurance that they are not completely losing the plot.

And when you do give advice, remember this:

Your advice is not automatically brilliant just because you are the mentor.

I know. Shocking.

Sometimes mentors completely miss the mark.

Sometimes the advice is technically correct but practically useless.

Like:
“You should network more.”

Fantastic.

Very inspiring.

How exactly?

At what event?

With who?

Good mentoring needs practical advice.

Not vague motivational pep talks.

If your mentee says:
“That sounds good, but how would I actually do that?”

…then the conversation is not finished.

That’s where real mentoring starts.

Practical execution matters.

Because good ideas without practical action are basically just decorative thoughts.

Final Takeaway for Mentors

One mistake mentors make is thinking they are the wise expert in the relationship.

Sometimes you are.

Sometimes you absolutely are not.

Your mentee has their own experiences, education, perspective, values, and understanding of the world.

And if you stay open, they will teach you things too.

Some of the best insights I’ve learned over the years came from people I was supposedly mentoring.

That’s the funny thing about mentoring.

If you do it properly, both people grow.

Final Takeaway for Mentees

And for mentees, here’s the important part:

Be honest.

You are not there to protect the mentor’s feelings.

You are there to build a relationship that helps both people move forward.

If advice is unclear, say so.

If something sounds good but feels impossible to execute, talk about that.

If the mentoring process is helpful but the advice isn’t a good fit for your situation, mention it.

Because good mentoring is collaborative.

Not performative.

And finally, if either of you needs more help building a mentoring process that creates real progress over time, have a look at the Mentoring Workbook and take 5 minutes to jot your thoughts down using this free resource. Sometimes, all it takes is that first small action to get things moving.

Just remember:

Good mentoring is not about sounding wise.

It’s about helping people move forward in practical ways that actually work in real life.