Colleges and universities increasingly seek to connect their alumni and students in mentoring relationships. But when higher ed professionals speculate about creating mentor programs, my reaction is: That’s really hard.

Not bad, mind you. But based on my experiences as a higher ed vice president for advancement from 2000-2017: very difficult. Why?

Here are 4 reasons:

1) Relationships HARD BECAUSE: Generally, relationships evolve. Most mentoring relationships develop this way, such that when the mentor (“I think I can help advise you if you like…”) or the mentee (“Would it be OK if you and I have these kinds of conversations every once in a while?”) become familiar with each other and establish enough common ground, one of those questions comes naturally and genuinely. Conversely, most alumni-student matching is done by assignment, which is bound to produce mixed results at best. That’s because matching is forced, typically informed by major, industry, geography, or a combination: good criteria for a first date, perhaps, but not enough to seed meaningful connections or the expectation of them.

BETTER PATH: Create dialogue first. Keep it simple. Think coaching. Ask students to write down two or three questions they have about their future. Share those with a few alumni and ask for responses. See what comes back. Smarter matching potential should begin to show up.

2) Timing HARD BECAUSE: Calendar is a challenge. Think about someone you know (and like) who you try to meet for lunch occasionally. You have to agree on date, time and location. Even when those details align, a last-minute glitch (illness or a work deadline or “I wrote down the wrong date”) could ruin your plan. Remember, you LIKE this person. Now, consider how the process might go with 2 strangers – an assigned mentor and mentee who don’t know each other – and they’re supposed to match calendars several times? That’s hard.

BETTER PATH: Set backstops. Have staff copied on initial communications so they can spot potential problems and jump in to solve. Position staff as helpers, not intruders.

3) Requirements (staff) HARD BECAUSE: This work requires managing many moving parts that involve people. Let’s imagine a wildly successful program in which 100 students are matched 1:1 with 100 alumni and everything is working great! The staff workload to support those 100 pairs will be enormous. Many of those 200 people will have questions or seek advice, mostly well-intended: “Can there be a meet-up in Chicago for all the mentors there who have mentees?” or “I’d like a second mentee” or “My mentor is coming to campus and wants to speak in my class” are predictable comments and questions that would need handling. If the staff response is to say “You’re on your own”, these participants, who should be the program’s biggest cheerleaders, will instead be saying “Geez, I’m spending all this time and you’re telling me you can’t even (FILL IN THE BLANK)”?

BETTER PATH: Start by determining what current capacity is for supporting your program and then aim to build it out to only 50% of capacity. So if you believe you can manage 20 mentor-mentee pairs, aim for 10 pairs, because there will be surprises and unexpected demands that eat up time. Prove you can handle 50% before you grow.

4) Making the case HARD BECAUSE: Building the case pushes many people out of their comfort zone. Most schools don’t make a solid case for mentoring. Instead, they assume it just makes sense, so everyone should get it, right? Wrong. You need to articulate in compelling and consistent ways that being a mentor or a mentee has value for participants. Alumni and students must see themselves in what you describe, and it may take several messages to get through, at which point you want their reaction to be: “Hey, that’s for me, I want to do that!” Conversely, many institutions ask alumni to complete a form to become a mentor, meaning the message is: we’ll take anyone. But the alumni you want – the ones who have the potential to be good at this – are busy. You have to compete for their time and attention. “Fill out the form” doesn’t compete.

BETTER PATH: If you are on the verge of creating a mentor program (or if you have one in place already), state or write (or re-state or re-write) the case for it and convince yourself it’s strong, appealing and worth the investment. When you are convinced, gather a few alumni and students and present the case to them. Invite their feedback, which will make the case even stronger. Plus, you’ll have some advocates.

These issues are challenging. Tackle them early and thoroughly, and you will be planning for 80% of the problems and questions that have potential to derail you. There will still be a surprise or two along the way, but that’s better than a couple dozen.