Making Your First Meeting A Success

While not essential to a successful mentoring partnership, it is likely that at some point you and your mentee will meet in person. Making the first face-to-face meeting feel safe, comfortable, and valuable doesn't happen by accident - there are things we can think about and do that increase the chances of a successful first meeting. Here's how to get it right. 

Find the Right Place and Time 

Where you meet matters. Pick somewhere public, busy enough to feel comfortable but not overwhelming. A café, community centre, or park all work well - particularly if it’s somewhere your mentee is already familiar with. Also think about accessibility - is it somewhere your mentee can get to easily? 

There are few things you should definitely avoid: 

• Your home or workplace 

• Isolated or quiet spots 

• Anywhere that feels too formal or intimidating 

Timing is obviously important, too. Daytime meetings tend to feel safer than evenings. Aim for about 45-minutes for the first meeting. It’s long enough to really connect, but short enough that neither of you feels drained. 

As always, the key thing is to be mentee-led. While you might be comfortable walking your dog in the park at 8am, or in that fancy new coffee shop, your mentee may not. By all means make suggestions - but be sure the time and location are their choice. 

Before You Meet 

Once the details are agreed, confirm them via text the day before, keeping things relaxed and friendly. Try something like: "Just confirming we're meeting at the café on Market Street at 2pm on Saturday - really looking forward to it!" This gives them a final reminder without making it feel formal or pressured. 

Be specific about logistics so they know exactly what to expect and can feel confident when they arrive. While "I'll be wearing a blue jacket and I'll wait by the main entrance" might feel like a line from a cheesy spy movie, it removes any anxiety about finding you or worrying about what happens when they get there. Encourage them to text or call if anything changes or if they're feeling unsure about anything. This simple offer of control can make all the difference. 

When it comes to money, there's no expectation that you'll pay for your mentee. If you do choose to buy them a drink or snack, keep it modest - under £5 - and make it feel natural rather than transactional. The key is to avoid money becoming an expectation or a pattern in the mentorship. If you're worried about this creeping in - or want to avoid the money question entirely - consider meeting at free venues like parks or community spaces. This keeps the focus on your relationship rather than on money, and it's a good way to model healthy boundaries from the start. 

Dos and Don’ts for the Meeting 

✅ Arrive early - you don’t want them waiting around and getting nervous. 

❌ Don't make it a big deal if they happen to be late. 

✅ Keep your phone nearby while you’re waiting - respond quickly and kindly if your mentee messages saying they are late or can’t find you. 

❌ Don't keep your phone out during the meeting - put it away once they arrive. 

✅ Be warm, relaxed and consistent - show up as the same person they've been texting with. Share bits about yourself, find common ground, and genuinely listen. 

❌ Don't make it feel like an interrogation - asking lots of questions in quick succession can feel uncomfortable and artificial. 

✅ Match their pace - some nervousness is normal on both sides. Don't rush into deep topics or expect them to be exactly as they are in texts. 

❌ Don't assume anything about their behaviour - if they're quieter than you expected, it doesn't mean they're not enjoying it. They're just adjusting to face-to-face communication. 

If They Don't Show Up 

Sometimes, despite good intentions, a mentee won't make it. It happens, and it's not personal. Send a warm, understanding message immediately: "No worries at all about today – these things happen! I hope you're doing okay. I'm here whenever you're ready." 

It’s important not to ask for explanations or make them feel guilty. Simply continue the relationship through texting as normal, and leave the door open for another meeting when they feel ready. 

After the Meeting 

Send a message later the same day saying something specific about what you enjoyed. Try: "Really enjoyed seeing you today - it was great to chat properly about…" This shows you were genuinely present and valued the time together. 

Keep texting between meetings and don't abandon your regular communication. Many mentees will want to continue messaging, and that's absolutely fine. The temptation might be to book something immediately or keep pushing for the next in-person meeting, but let the connection breathe a little. Go at their pace instead, and celebrate the progress you've made so far. 

Remember: Mentee-Led, Always 

Not every mentoring relationship will include regular in-person meetings. Some will flourish through digital communication. Others might find a rhythm of occasional meetups alongside texting. All of these are equally valid and valuable. 

Your job is to create the conditions where trust can grow and to follow your mentee's lead every single step. Be patient, stay consistent, and celebrate the progress - no matter how small. Every moment you show up - however your mentee prefers to connect - is an investment in their future. 

You might also enjoy this article about Conversation Starters With Your Mentee.