In my first company, I tried to act extroverted, because I thought that’s what good leaders did. It was exhausting and counter-productive. I’ve found a more comfortable way of working and wanted to share a few thoughts and resources that have been helpful to me.
The back-thumping, rapport-building, steak-and-strippers salesman is just one of several styles, and it’s not even the most effective. In fact, it tends to be actively harmful if you’re developing long-term relationships (like in large sales, long-term partnerships, and fund-raising). For all the research on this, check out SPIN Selling by Neil Rackham.
The turning point for me was realising that it’s okay not to have all the answers. People hate when you go in with the shiny presentation and the hard pitch. Rather, being willing to set aside your ego and ask lots questions is the single most important thing you can bring to the table. I didn’t have to be sleezy and I never needed to sell people something they didn’t need. Instead, I just had to spend the time to deeply understand their problems. If you want to go deeper into question-asking, I wrote up my learnings in The Mom Test.
And finally, not all sales is created equal. I’m pretty comfortable in a meeting these days, but I’ll never be happy making cold calls. Knowing that, I’ve spent extra effort getting warm intros and inbound leads. You don’t need to fight every battle or live up to someone else’s standards of what a classic salesperson looks like.
I like YC’s attitude on pitching to investors: it doesn’t matter how awkward you are, as long as your startup is good enough. And if your startup is bad, the smoothness of you (and your pitch deck) are irrelevant:
The one point I wanted to make before we get started is, we actually don’t spent a lot of time at YC focusing on this. The main reason is the best way you can make your pitch better is to improve your company. If you have traction and your company is doing well, these conversations are like… the investors want to see you succeed. So if you remember anything, it’s make your company better and your pitch will be easier.
PG wrote a great essay on how to convince investors which goes into a bit more detail. And to see how simple a good investment pitch really is once your company is good enough, check out the video below (timestamped to ~20:50).
When you feel like you’re being judged on some sort of performance, it can be kind of weird. But once you realise that you’re just trying to mundanely explain what you’re up to (and will be judged on the numbers rather than your level of zazz), it gets a lot less mysterious.
The myth that leaders are charismatic comes from the fact that MBAs are charismatic. And the reason isn’t because that makes them better leaders, but rather because due to a historical quirk, that’s what business schools select for. Plus, people who talk more are perceived as more intelligent, but that doesn’t correlate at all with better results. In team scenarios, a loud leader tends to clobber the expertise of his or her group rather than utilise it. And within the high-power corporate world, the self-promoters do tend to get the promotion.
In Good to Great (which I don’t really recommend as required reading for startup founders), author Jim Collins remarks how surprised he was to find that all of the top performing companies her reviewed were led by introverted, unassuming leaders who made great use of their team’s skills rather than their own. Quiet by Susan Cain touches on the rise of the myth and gives a summary of the data throughout the first few chapters
Having an office is probably my least favourite part of having a company. It took me an embarrassingly long time to realise that:
- I don’t need to be in the office all day
- The office doesn’t need to be open-plan
- Nobody else needs to be in the office all day
- Fun around the water cooler is not a required part of the workday
I went to an extreme and my current business is fully remote with no office, but I recognise that’s not always possible (and expect we may need an office sometime soon as the team grows). But now that I know what I need, I no longer fear it. I’ll work by myself when I’m working on focus tasks and join the others when necessary. I won’t worry about putting in face time. If I have an office, I’ll put a couch in it so I can have a quick nap when I’m feeling drained. This is how many of us work effectively at home, and yet we willingly throw it away as soon as our business starts succeeding.
There are certain drawbacks to the office setup mentioned above, which is that sometimes people won’t be around when you need them. So we need to deal with remote working at some level. The golden principle comes from Remote by 37s (which is a fun read but not exactly groundbreaking beyond this one key point).
Remote is a first class citizen.
This means that if you’re going to do any remote working, then you need to take it seriously enough that those working away from the office don’t become marginalised. For example, if decisions are made during an impromptu meeting, then the thinking and results need to go into the chat log or dropbox for remote team members to review. And you need to be willing to spend a little money on good tools like a reliable conference calling setup (we just use freeconferencecalls.com, which is surprisingly robust for small teams).
Being remote-friendly (for some portion of the time) is probably the biggest way to improve life for introverts, whether that’s you or your team. Incidentally, I’ve also found that it helps the team get away from an urgency-driven culture and keep everyone focused on longer-term priorities.
Some uncomfortable situations where charisma matters are too valuable to pass up (e.g. networking event with tons of potential customers or partners). In those cases it’s useful to be able to pretend for a while. My favourite book on this is The Charisma Myth by Olivia Cabane. While/ the subtitle makes it sound like cheesy positive psychology, it’s fairly data-driven in the way it breaks down the myth that charisma is a born-with-it-or-not sort of in-built trait.
Instead, charisma is judged based on a few behaviours which are relatively easy to mimic. Turns out that the divide between “pretending to be charismatic” and “being charismatic” is far more permeable than most would have guessed.
When I know I’m out of my depth, I keep a close eye on my reserves of willpower. If I start feeling drained, I’ll head outside for a walk and a coffee, or go find a quiet nook and make myself look unapproachable with headphones and a book. If you haven’t read it, I highly recommend the excellent Willpower by Baumeister and Tierney (even if you’re already sick of the constantly overused marshmallow experiment results).
Startups are kind of weird-looking to begin with, and as a founder, you’ve got the incredible opportunity to mould it even further into exactly what you want it to be. You don’t need to act like some other company just because they’re famous. If the mainstream way of doing things isn’t for you, try something else. You’ll be happier for it, and you may be surprised how many other people on your team appreciate the change as well.
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