The fact that the one-line summary of this article is “Ignore all the instructions and just do what you think is right” is unlikely to surprise anyone who knows me.
At the end of the day, great relationships are built on authenticity and accurate empathy, so you need to lean on your personality and unique life experience to foster genuine human connections. My hope is simply to convince you to be your own version of a real human person. How you go about doing that is up to you.
I’ve read hundreds of books on communication skills, management, relationships, the works. I’m a qualified doctor; at medical school I was taught conversational structures and emotional vocabulary for how to take a history from a patient, how to break bad news, how to engage people who are having the worst day of their lives, even how to apologise. In my academic then professional working life, I’ve been fortunate to go on dozens of training courses covering communication skills. I’ve benefitted throughout from wonderful role models and mentors who have shared wisdom and set fantastic examples.
What I’ve taken from all of this is that at some point you just need to take all the books, the education, the theory, the feedback, the well-meant advice, and the role modelling, and put them in the bin; and then find your own way regarding how to, gasp, deal with other people.
Thankfully the stakes are usually lower when mentoring or managing than doctoring, but in my experience the same principles apply to these activities and indeed to many interpersonal situations: show up as a real human person; be authentic; bring your personality and be willing to use it; tailor your approach uniquely to the person and situation in front of you; only ask questions you care about the answers to; and trust your intuition when it tells you to roll up your sleeves and get stuck in.
Here are nine principles I believe are crucial regarding building great relationships as a mentor and manager. To keep wording clear I’ll use “mentee” throughout because many leadership roles have mentorship in common. I’ll offer some parallels from my time in medicine, and some examples of me getting things horribly wrong (and occasionally right). And yes, I do see the irony in offering up this advice! I fully expect much of it will (rightly) end up in your personal lifetime advice bin along with everything else you’ve heard. You are your own human person after all.
And finally: to all mentees and mentors past and present, I’ve taken some narrative liberties with the stories I’ve used to illustrate my points, but if you recognise yourselves in my cautionary tales, I hope you can think benevolently of me!
Give your mentee time and attention
This is the most fundamental thing. It sounds boring but it’s really not.
Be ultimately reliable. Trust doesn’t come from grand motivational speeches: it’s built through small actions over time. It’s not about tools or techniques; it’s about character, and your way of being in the world.
Schedule sessions (actually preferably get them to for ownership) with the mutual expectation that neither side will request to change the time. Put serious effort into not cancelling or moving sessions. Rescheduling is sometimes unavoidable, but the psychological safety that grows from being able to rely on your mentor in a logistical sense is wonderful. In over three years of fortnightly meetings with my career mentor I reckon we’ve skipped fewer than ten sessions, including their parental leave, and rescheduling is rare. I really appreciate this. The nature of my job means my own schedule can be somewhat chaotic, so I do reschedule meetings with mentees sometimes, and more often than I’d prefer to; but I feel the cost of this and try hard to avoid it.
When you’re together, be fully engaged and committed. If you’re online then messaging apps must be closed, and if you’re in person then sit somewhere out of sight where you won’t be disturbed and don’t bring your phone. Don’t meet when you’re on call or expecting your groceries to be delivered or something.
If you only have a little time to give them, still give it freely. Make sure they feel like your priority. Don’t constantly go on about how busy and important you are.
Take charge of timekeeping and pace. Some mentees will do this themselves automatically, but you should have a strong prior that this is your responsibility. Don’t let something heavy come up five minutes before the end when it can’t be given proper attention and time to settle afterwards.
Never cut sessions short, and don’t overrun even if you’re both free. Varying the timings without notice creates a sense of uncertainty and lack of control. You want the opposite.
This point comes down to treating someone with respect, that is, being a real human person.
Give your mentee agency
Giving someone agency means helping them feel in control of their stake in the relationship: like they can influence what happens, and like they can handle anything that comes up. A sense of agency helps someone feel psychologically safe. It means they can be fully present, and they can be flexible.
What each person needs in order to feel like they have agency will be almost unique. Rather than applying blanket so-called “good advice”, which as you’ll predict I don’t believe in anyway, give your mentee agency by putting their true needs at the centre of the relationship. This means different things for different pairs of people and at different times.
Sometimes putting your mentee’s needs first means being gentle and positive, asking endless questions, letting them shape the agenda entirely, and not telling them anything hard to hear. Other times it means doling out the odd good healthy dose of benevolent paternalism. Some people are at their best – or most self-actualised – when arguing with me about something[1]. It’s like this in medicine too. Some patients want to lecture you about what’s wrong with them then criticise all the advice you give them, whereas others complain if you ask them what they think is going on, saying things like “Why are you asking me, you’re the doctor!”.
In terms of the physicality of meetings, some people can only engage on a personal level when face to face. Others love meeting online as it feels professional but can be less intense than meeting in person. Others might do best when cosied up together on a sofa with a cup of tea. Some people open up like flowers in the sun if you go for a walk together instead of staring at each other over a table in a joyless meeting room.
It’s up to you to divine how your mentee will flourish best in the relationship, but all the choices, both explicit and implicit – all the agency – lies on their side. Depending on how naturally reflective your mentee is, you might be able to just ask them directly what they prefer, but be prepared to experiment regardless.
Genuinely having your mentee’s best interests at the heart of everything you do is the key.
Give your mentee firm and enthusiastic cheerleading
Very often, all people need is to be told that they’re doing great! Some loud cheerleading can be fundamentally transformative, and in my view is woefully sparse in professional culture. In an upcoming article, I’ll tell you how I’ve implemented Snap Cup (from Legally Blonde 2!) in various of my teams over the last few years.
Spewing generic compliments obviously isn’t good enough, and can be actively damaging to your credibility, but getting fully on someone’s side to the point where you can see them and celebrate them properly can be a highly invigorating thing to do. Praise should be mainly for effort and behaviours rather than for traits, because those can be controlled, but don’t hold back from sharing how enjoyable you find your mentee separately to how accomplished and impressive they are.
Positivity definitely doesn’t mean blanket, non-specific agreement. If all you ever say is “Whatever you think is fine, that sounds good, go you!” then you’re withholding the thing you have that they don’t: your wealth of lived experience, namely your opinions, and how you acquired them. Which brings me on to…
Give your mentee the benefit of your distilled, focussed experience
We’re not all the same. Two people going through the same set of experiences won’t take the same learnings from them. This is great. It further suggests that you should tell the truth, warts and all. Being as honest as possible when sharing your own reflections increases the chances of another person being able to apply your experience to their own situation, so holding back misses the point.
But no one needs to hear your life story. It’s your job to extract the important details and bring them to bear on the topic in hand. Sometimes this means skipping the bits you yourself find the most interesting – become fine with this! I still cringe to remember a chat I had with a new mentee a few years ago, where I bored her absolutely senseless with a several-minute monologue about some situation I was in. The other large mistake I made here was doing this right near the end of our allotted time, so when I finally stopped talking she was like “Okay, I have to go now”. Mortifying.
A saying from medicine: the best treatment is the one the patient will take, meaning that sometimes it’s better to prescribe the second-choice drug that only needs to be taken once per day instead of the first-choice one that needs to be taken six times per day. Pills that stay in the packet have no chance of helping patients. And there’s no such thing as “good advice” in a pure sense; there’s only advice that has a chance of affecting people, which is specific, relevant and tailored uniquely.
The last thing I want to say here is that sometimes you really do need to tell people things. Non-violent communication is a worthwhile tool to have in your artillery, but it’s not the only one you should ever use. While most advice is more of an FYI – a take-it-or-leave-it kind of thing – sometimes you need to commit and exert a bit of precisely judged force on a situation. Learn to do this with authenticity and compassion and you’ll grow stronger relationships.
Give your mentee tea and empathy
Sometimes a kind, listening ear is all that is needed, not problem solving. You should learn urgently to tell the difference if you don’t know this already.
Your mentee won’t necessarily be aware that they want empathy rather than solutions. Opinion is divided on how to handle this: some people enjoy being asked upfront whether they’re after empathy or advice, whereas myself I find this quite confronting when I’m in a mess, and end up panicking about not knowing what I wanted because confusion was the nature of my mess. As usual, the best way to find out how someone likes to handle themselves in crisis is to observe, gently ask, experiment, then reflect together afterwards.
Give your mentee the chance to genuinely interest you
Question style and active listening is a vast topic and one that truly fascinates me. I’ve swung wildly in my approach here, from my early days of neurotically thinking I had to say declarative things to provide any value through to “Ask as many questions as possible, preferably open ones”. As with all dimensions, I think you need a bit of everything.
In medicine, asking patients too many open questions gets you stories about cats and photos of grandchildren. Doctors eventually learn to ask one or two good open questions at the start of a conversation, not just to show the patient that you care about their story and that you’ll let them say their piece (even the most garrulous people often quieten down once they trust they’ll be allowed to talk!), but mostly because people really do often have all the answers themselves and you’d do well to listen. But once you’ve got the exposition out of the way, deploying some clarifying questions then progressing to more focussed, targeted questions extracts the information you need, and risks fewer derailing cat stories.
The skill that comes with experience is knowing what kind of question is most likely to get you where you want to go. The same goes for mentoring. Some people really realllly like to talk – counting myself amongst that number here! – so find a way to let them talk while steering things in a useful direction by appropriately varying your question style.
But whatever else happens, you absolutely must stop them talking before allowing them to bore you.
If you ask a question “just for the sake of it”, maybe because you read it in a book once, you are almost guaranteed to be bored by the answer, which is highly unfair on your mentee. Allowing someone to bore you is phenomenally rude. Coming up with questions you genuinely want to know the answers to is the only humane and worthwhile choice. You can’t fake finding someone interesting – you just have to find them interesting! So get it done.
Most people enjoy being asked good questions! But bad questions can be highly off-putting. Few questions are inherently “good” or “bad” – what makes them so is context and conviction.
More personal cringe here: I once asked someone – slightly on autopilot – “What’s your approach to time management going to be on the project?” and they looked at me like I’d just crawled out from under a rock and repeated the question slowly in head-shaking disbelief.
This was a ‘bad’ question, from me, not only because I didn’t care about the answer, meaning I was actively inviting my mentee to bore me, but also because I just don’t talk like that, meaning my mentee was highly aware I was just phoning it in at that moment. Someone else might be fine to ask this question authentically; it all depends on what kind of real human person you are.
With my brain engaged, I’d have probed for any nervousness about the breadth of the role, or maybe opened a conversation on the philosophy of delegation.
You can only be interested by someone if you show up and bring your personality. Giving people the chance to interest you is the human thing to do. Being bored is your fault, your choice, and unforgivable.
Give your mentee the power of your network
Introduce your mentee to as many interesting people as you can. Not only does this put them more directly in the way of interesting career opportunities, but it also increases the number of new formative opinions and ideas they’ll be exposed to.
Always be on the lookout for opportunities for your mentee. At a consultancy like Softwire, this means actively considering them for every interesting-sounding role you ever hear about, and then selling them to the person resourcing the project if you think they might be a good fit. This might also mean proposing them for interesting initiatives and bringing them into organisation-level conversations where they’d be interested and useful.
Talk your mentee up to other people! Let the world know why they’re great! Never say anything that isn’t true, of course, but it’s your job to raise their profile in whatever way is most useful to them.
Call in favours for them. I’ve leaned on various colleagues over the years to get my mentees more focussed advice than mine when needed, for example arranging a nascent Tech Lead weekly conversations with a seasoned and respected Principal. The other side of this of course is that you should be generous regarding putting yourself out for other people’s mentees too.
At times in my life it’s felt like great opportunities just happened to drop out of the sky. Looking back I can see that I had a big surface area in the world via the size (and power) of my network, but mostly the networks of my mentors. You can share your network’s power with others. Effective networking increases your mentee’s surface area so they can benefit from more serendipity.
Give your mentee absolute confidentiality
Other than the normal things that can’t stay confidential (like the potential for harm to themselves or others, serious misconduct, breaking the law and so on), your mentee should have total faith that what goes on in the room stays in the room. I find it helpful to be absolutely explicit about confidentiality (thanks medicine).
It’s always worth exploring why someone wants something to stay confidential between the two of you. Sometimes you can help mentees overcome built-in resistance to the principle of being more open with other people; it can be in their interests to be slightly more open than they might naturally be comfortable with. After all, no one can do them any favours if no one knows what they want. But exerting any (and it must be gentle) force here takes tact and judgement. Don’t assume that sharing is always better if only they’d agree to it. Putting your mentee’s needs at the centre of the relationship means taking each person in their own context and doing the right thing by them.
Give your mentee criticism from a place of love
This is absolutely your job, and you’re letting your mentee down if you shy away from telling them things they need to hear simply because doing so is hard. Done right, criticism and pushback are gifts. But your communication skills, empathy and basic human decency need to be on point.
There’s a whole other article in here about how to seek and give feedback effectively and humanely, but the simple truth is that you just have to get it done, whatever it takes. You need to be accurately empathetic to your mentee’s internal world in order to give effective loving criticism. This takes work. If you’re not properly bought in, the trust between you is compromised, and at best your advice won’t land and at worst you could really hurt someone for no gain.
If your motivations aren’t right when it’s time to offer someone difficult feedback, then don’t do it, and consider getting them a new mentor pronto (or at least find someone else who can have the difficult conversation in hand). You should only put people through difficult things if you care about them, and have a relationship based on honesty and empathy to build on.
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That’s all from me for now. You can tell that relationship building is something I’m truly passionate about, so please come and talk to me if the same goes for you, whether you agree with what I’ve said or not – in fact especially if you don’t. And if all I’ve achieved with this article is you thinking “God, I don’t want to be that kind of mentor” then great, go forth and be a different kind of real human person! And then please come and tell me all about it.
[1] I have one mentee who regularly requires a 40-minute debate to concede that logically there could be something to be gained by trying whatever it is I’m suggesting. What the actual thing is that I’m suggesting never matters here.
