Category Archives: Business

Personal update: I helped launch a new venture capital firm this week called Village Global. You can check out the Village site, or read our announcement post.

Exciting adventures ahead!

“Don’t be transactional. Build genuine relationships. Play the long game. Don’t keep score. Give first.”

All good advice when building your professional network. The Start-up of You is full of these sorts of lines. But good advice taken to the extreme becomes bad advice.

Here’s how. Say you want to maintain a relationship with someone busy in your network. Heck, maybe you even have a specific question or favor to ask of that person. But you don’t want to seem transactional. After all, “authentic” relationships in business involve mutuality and back-and-forth and personal rapport. You don’t want to come off as having a transactional agenda. Right? Right.

So you ping this busy person in your network and ask if they want to “catch up” with you sometime for coffee: “It’d be great to see you and catch up on life. Let me know if you are around next week?”

Unless the person is already a pretty good friend of yours, the answer you often get back is… Crickets.

What happened? The random coffee catch-up meeting request is the most common “external” meeting request in the world, largely because so many of us have been trained to not seem overly transactional when we stay in touch with our network. So when we reach out to busy people, we bury our agenda and hide behind “coffee catch up” as the vague purpose of the meeting.

The problem is, busy people are busy. In fact, they get hit up for coffee catch-ups multiple times a week. They can’t take coffee catch-up meetings all day. They actually have to get real work done. So they avoid your request for random coffee.

What will catch their attention instead? A specific transaction or topic.

“I’m considering taking this job opportunity and would love your perspective.”

“I saw you on stage at a conference and had some feedback for you on the virtual reality topic you spoke about.”

“I’m hosting a conference in a month and would love to brainstorm who we should invite as speakers.”

Best case, this transaction intersects with something they’re actually interested in and would fine useful. Medium case, it lends a finite crispness to the interaction — it feels “manageable” — and the person is likely to agree to a quick call or meeting if he knows it can be quickly resolved. Worst case, the topic isn’t of interest to the person at all — in which case, didn’t you both just save time by realizing that on the front end?

Oftentimes, when reaching out to someone busy, you’ll have a specific transaction in mind plus an interest in just general catch up and general relationship building. In these cases, consider leading with a “transactional bluff.” Lead with the transactional item you have in mind, but know that you may spend 90% of the meeting — once you’re actually in the meeting — talking about whatever general catchup topics you want to cover. Maybe you spend the first 10% of the meeting on the transaction and then you switch to “How can I help you?” and the other practices that fuel long term relationships.

Bottom Line: Busy people need a reason to prioritize scheduling your “catch up” meeting. If you don’t know someone well already — this means most people in your professional network — be candid about a specific transaction you have in mind when making the meeting request.

A friend asked me via email if I’d be open to introducing him to another busy friend of mine. He then wrote:

If you are willing, and feel you could recommend a meeting with sincerity, then I’d be most grateful for an introduction. And if you have the slightest hesitation, please do nothing. In my mind, the latter choice is the default, so please know I have zero expectations.

I really liked the way he put this. It feels very low pressure. I’m going to start using the phrase “If you have the slightest hesitation, please do nothing….please know I have zero expectations.”

All business is people business ultimately, and so improving your ability to size someone up should be a relentless priority — it is for me, anyway. By “size a person up” I mean figuring out how much you trust a person, how you can best collaborate with him, whether you’d hire her, whether you should fire him.

One of the simple ways I size a person up is by understanding how they understand and judge other people. In this way, I start to be build a model of the person I’m getting to know. I get to know their likes and dislikes, their biases, their underlying motivations, and of course their meta ability to evaluate people — all by hearing them talk about friends I know well.

Practically speaking, when I meet someone new, I like to ask them about someone we know in common. “So how do you know Jane?” Sure, it’s a trite question. But it can lead to a substantive exchange. It doesn’t have to be gossip. How has this person partnered with Jane? What’s frustrated him about Jane? What have been the delights?

When you ask someone to talk about their relationship with someone else, they often inadvertently reveal a lot about who they are.

At a breakfast meeting, I once asked an acquaintance — who I was also evaluating as a prospective business partner — to describe how he knew a mutual friend. As I probed, I realized this acquaintance spoke in condescending, patriarchal terms about a person who I very much considered his peer. It was revealing. I may not have gotten a glimpse at this element of his oversized ego if we had not gone down this path.

In another case, by talking about mutual friends I realized the person I was speaking to grasped subtleties about a friend’s personality that I had missed, and it made me all the more excited about partnering with him because of his extraordinary ability to make sense of at least one complicated person — and likely many others.

Bottom Line: Get to know someone new by asking him or her about someone you already know well.

It’s hard to give advice to a peer or an especially prideful person of any sort. Advice giving can be interpreted as a power move, and if you don’t deliver the advice in the right way, the other person — a colleague, a partner, someone who’s close to you in terms of professional trajectory — can feel subtle resentment. Even if he asks for your feedback, a part of him is asking himself: “Who are you to be giving me advice?”

I handle this in two ways.

“I’m Trying, Too.”

Make your advice come off as less condescending by acknowledging your own on-going quest to live up to it or your own on-going need to be reminded of it.

In her brilliant book of advice columns, Tiny Beautiful Things, Cheryl Strayed writes to a reader:

You need to stop feeling sorry for yourself. I don’t say this as a condemnation–I need regular reminders to stop feeling sorry for myself too. I’m going to address you bluntly, but it’s a directness that rises from my compassion for you, not my judgement of you. Nobody’s going to do your life for you. You have to do it yourself, whether you’re rich or poor, out of money or raking it in, the beneficiary of ridiculous fortune or terrible injustice. And you have to do it no matter what is true. No matter what is hard. No matter what unjust, sad, sucky things have befallen you. Self-pity is a dead-end road. You make the choice to drive down it. It’s up to you to decide to stay parked there or to turn around and drive out.

She literally says: “I don’t say this as a condemnation — I need regular reminders to stop feeling sorry for myself too.” And that’s what makes it work.

Another example. Recently, a friend on Facebook recently wrote about how she is grappling with critiques of her personality. Another friend — who’s her peer, not an anointed Wise One — commented: “Be yourself, because your self is awesome. Trite to say, a lifetime to try to do. I know because I’m also trying.”

I know because I’m also trying. That’s the sort of advice given by a friend who’s a peer.

From “You should…” to “I would…”

The second approach I take when giving advice to a peer or prideful person is I avoid directly addressing their scenario and instead I make it about myself. When you find yourself saying “You should do X…” you begin to trigger people’s pride instincts. Even if they asked you directly for advice, by directly telling them what to do, you risk unleashing subtle but very real swirls of resentment.

So if you tell me about an employee you’re trying to hire and a dilemma you’re facing in the hiring process, and ask me what you should do about it, I would talk about a similar experience I’ve had and how I handled it, or construct a hypothetical parallel experience and talk through what I would do in that scenario. I’m avoiding the phrase “you should do X, you should think about Y.” I’m instead saying “I would be doing X, I guess I would be thinking about Y, I wonder about Z…” I’m trusting in their ability to connect the dots between my experience or my constructed parallel scenario and their own situation.

Note that for people who are clearly my junior, or where I do not fear at all any status offense, I will sometimes be quite direct in my advice. But relationships with peers at work and the associated status considerations are rarely quite that simple!