Tools #Maddy101
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31 March 2020

How entrepreneurs decide which meetings to take and which to ditch

Joe Procopio shares his wisdom to help you avoid lost time over useless coffees and identify the real opportunities.

I still take too many meetings. Even after 20 years in the business of being an entrepreneur, I wind up booking at least one useless meeting a month. I’m probably not going to change my ways because I’m at a point in my career where my radar is probably as finely tuned as it’s going to get, and wasting an hour here or there is no big deal.

Let that be my first point: Being an entrepreneur isn’t a laser-focused vocation. Far from it. I personally know a few successful entrepreneurs who never have time for anyone. Don’t become that — it’s a rough way to live.

At the same time, the vast majority of entrepreneurs drown themselves in meetings, phone calls, events, webinars, and pointless social media exchanges. There’s no reason to live like that either. So I’m going to give you a guide for these manoeuvrers:

  • Getting over the feeling that every chance encounter could be an opportunity
  • Deciding where your precious time should be spent
  • Politely turning down a meeting without burning any bridges

Because there’s definitely a balance between drowning in meetings and being a meeting Scrooge.

You are spending your time

Entrepreneurs are programmed to believe that opportunity lurks around every corner. But that programming gets problematic quickly.

Let me put it this way: What if I reached out to you said, “Hey, I’ve got something I think you should buy. It’s $20.” Now, my mystery offering could be something cool and valuable. But it doesn’t matter — you’re not going to spend $20 without knowing what you’re getting in return. But we entrepreneurs constantly spend our time that exact way.

“Can I get 30 minutes of your time?” is a common ask, but 30 minutes here or an hour there quickly adds up to a lot of wasted time. Yet we rarely ask what we’re getting for our spent time before we spend it.

Help vs. business vs. curiosity

The first thing you need to do is categorize the meeting request — even if the request is coming from you. This is the equivalent of figuring out what you’re getting for your spend. Once you know that, you can decide to spend time or not.

There are basically three types of meetings:

  • Help: One side needs something from the other
  • Business: There is mutual benefit for both sides
  • Curiosity: There is interest on one or both sides to learn more about the other

Any other reason to meet is kind of a waste of time, as cynical as that sounds. I’ll redeem myself by reminding you that earlier I said I don’t mind wasting a little bit of time now and then. And I’ve always got time for my friends.

Outside of work and friends, all my meetings slide into the help or curiosity categories. At work, most of my external meetings fit the business category, but I get more than a few curiosity and even a couple help meeting requests.

It’s not that hard to categorize, but it can get awkward.

The bait and switch

I have a hard time saying no to people, especially when they need help. I’m okay with that. But it took me a while to figure out that some of those people couldn’t be helped by me. Worse, some people didn’t really want my help — they wanted something else, like my money, my connections, or my endorsement.

At work, the external bait and switch is constant. The business or curiosity meeting is the bait, but what’s really behind it is something they want from me without too much regard for what I need. In other words, it’s one-sided, but of course, they’re not going to say that. So I ask.

Email screening is your friend

I don’t ever want to miss an opportunity. I don’t ever want to be cynical. And I like to help. But I don’t ever want to be baited and switched. So I use an email screening tactic.

For any meeting you categorize as a business, email first and ask if they have some direct questions they’d like answered and ask how they believe you can help them. This will do a few things:

  • It will obviously help prepare you for a better business meeting
  • If it is indeed a curiosity meeting, they’ll say they want nothing (up to you to believe them or not)
  • If it is indeed a help meeting, you can determine whether or not you can help
  • It will show whether or not they’ve spent any time thinking about why they need a meeting with you
  • If all of the above is false, you have the opportunity to answer their questions, push them in another (more proper) direction, or politely decline with a valid reason

The reverse is also true. If you can’t ask direct questions of the person you want to meet with and if you can’t frame an objective ask of what you want from the meeting with that person, you likely don’t need to request that meeting.

A couple of side notes:

  • I’ve never realized an opportunity that started with “I can’t really put it in an email — phone or face-to-face is better.” I’m not a spy
  • “I just want to pick your brain” means there’s a sales pitch involved
  • Big-shot business people are not above the bait and switch. I could totally drop some names of folks who have asked me out of the blue for a phone call, and I jumped at it, and it was like 90 minutes of bullshit

Prioritise your meeting time

Here’s a quick guide to spending your external meeting time wisely:

Customers and prospects

You want to meet with all of them, of course, so try to suss out who is fishing and who is serious before you take the meeting. Despite conventional wisdom, customers like questions. In fact, they may even appreciate the fact that you’re trying to determine if they need you or not without the timesuck of a sales call.

Employees and talent

If someone wants to work for you, you want to take that meeting. But try this every once in a while: Say no, then see if they come back. A lot of folks will desperately want to work at your startup until they get a peek behind the curtain. Don’t let that first peek be their first day of work.

Partners and vendors

Be wary. Most of the potential partner meeting requests I get to start out all heated until something shinier comes along. And all vendors have sales quotas. Make sure you know exactly what you need from a vendor before you take a meeting.

Venture capital firms and other sources of funding

These are always exciting meetings to take until you get there. Then they can be a ton of talk with no movement. So let me just say this: You’re either raising money or you’re not. If you are, take every meeting you can. If you’re not, shelve those meetings until you begin a full-time fundraising cycle.

Events and webinars

Let’s throw these into the meeting mix as well. Pick one event or webinar a month that you want to do. Truth: Most events and webinars aren’t for the attendees — they’re for the organizers and sponsors. Give every event and webinar one chance, don’t be afraid to bail and don’t return to something that didn’t provide value the first time.


A lot of my external meetings these days are excuses to get coffee or beer with my friends in the industry. These “meetings” always have value, but make sure you keep a balance.

How to say no

There are a ton of ways to say no without looking like an ass. All of them involve the truth, and there’s never a good reason to be impolite. Here are just a few of those ways:

  • Using the email screen I laid out, offer what you can over email at your pace and on your time
  • Using what you learn over the email screen, politely state what’s in and out of your domain of expertise or order of priorities
  • Thank them, let them know you’re not interested, don’t elaborate, wish them well
  • If the request makes it obvious that you were just a name in a long list of emails sent out that day, just delete it and move on. Don’t get snippy

When you’re trying to build something greater than yourself, your time is indeed precious. In an ideal world, we can peek around every corner and lift every stone, but at the end of the day, every minute we have needs to be spent working on the mission. As long as you’re confident a meeting fits your mission, then, by all means, take it.

This article was originally published on Medium by Joe Procopio

Joe Procopio is a multi-exit, multi-failure entrepreneur. He is currently the Chief Product Officer at Spiffy, a startup focusing on on-demand vehicle care and maintenance. In 2015, he sold Automated Insights to Vista Equity Partners. In 2013, he sold ExitEvent to Capitol Broadcasting. Before that, he built Intrepid Media, the first social network for writers. You can read more and sign up for his newsletter at