6 ways to be a better startup boss

I’m probably not a very good boss.

And for someone whose title is “CEO of RampTshirts.com”, that’s not a great endorsement of myself, right?

So, I’m committed to becoming better. I’ve employed people on and off in various capacities since my early twenties. But I’ve never once really considered it to be something I had to “work on”. I just assumed that as a “good guy” (I hope), it was something that would naturally mean that people would trust what I’m saying, and understand my vision. But that’s just not true.

As a music producer I would spend hours honing my skills in Logic and Cubase. As a startup founder I have spent hundreds (thousands?) of hours reading blogposts about Facebook ads, growth hacking, how to “game” Product Hunt, Crunchbase and AngelList. And as an event organiser I’ve spent days reading about project management and ways to increase attendee satisfaction. So surely it stands to reason that I should have spent the same, if not more, time developing my skills as a people manager.

But I haven’t.

And I’m aware that I’m probably typical of startup founders in that I’m happiest when I’m head down in my laptop “Getting Shit Done”. And that means I’m not always aware of those around me, how they’re feeling, and what they need from me.

So, I’m going to list below some of the things I’m doing, and what I’ve learned over the recent weeks of trying to be a better boss and manager. And I’d *love* to hear and incorporate any of your thoughts and resources you can point me to (leave me a comment!). So much is written about raising seed rounds, exits, getting in TechCrunch etc etc. But so little about how to be a better boss in a startup.

This post will very much be a living document for myself and others.

1. One-On-Ones

I signed up for Duuoo, a “smart assistant that helps develop manager’s skills”. I found two guides they’d published (How to Become a Better Leader with 1-on-1s, and How to Be an Effective Leader) when I was Googling for advice and “templates” to help me run an upcoming 1-on-1 with our first staff member in our new office in Sofia. Alongside the language and cultural differences, I’m aware that a first (and very belated) 1-on-1 can be challenging for both parties, so I want to make sure I do a good job, and reassure her that I’m impressed with her work, as well as being 100% open to any feedback and criticism she has.

Duuoo integrates with Slack to help you prepare for review meetings with staff by managing both of your calendars, and asking preparatory questions which will create the framework for the meeting.

The above staff member filled out her responses to the prep questions earlier today, and already I’m actually kind of looking forward to our first 1-on-1 next week, rather than dreading it!

2. Free courses

I’d signed up for Highbrow a few months ago (a free email course programme that educates you on pretty much anything from Improving Photography Skills to SEO Fundamentals by sending you a quick email a day for 10 days on your chosen topic). Their course “How To Be A More Mindful Leader” piqued my interest, and I’m currently 8 days in. I must admit that trying to learn from my inbox isn’t always the best for me, as it sits among countless other emails clamouring for my attention. So I normally open the email as a fresh tab, archive the email, and get back to it later in the day.

3. Mental health and “self-development”

I’m sure someone once said that to be a good leader you have to know yourself, and be comfortable with who you are. And that’s something i’m continually trying to do. I’m a pretty rational person and usually find it difficult to discover content on this stuff that is empirical, and not full of “woo”. I have a lot more faith in a double-blind study on the efficacy of mindfulness than I do in someone telling me to put a crystal on windowsill and get a dose of homeopathy.

A few years ago a friend sent me this video of investor/coach Jerry Colonna talking about how to not “disappear into the fire”, and get consumed by your startup. It’s an hour long, but it’s very worth it. I watch it at least once a year. We all work in/on startups because we want to live better, more fulfilling lives. But that’s no good if you push yourself to breaking point. And you can’t be a good boss if you’re broken.

This is a great interview with Jerry, too:

Also worth checking out is Sanctus, who believe that we should treat our mental health like we treat our physical health. Which I 100% agree with (and am also pretty bad at doing — i’ll regularly go out running and walking to keep myself fit, but I can’t remember the last time I meditated, did relaxation exercises, or just completely shut myself off from the constant ping of emails). They have a mix of community events, videos, training sessions etc, and come from a background of wanting to improve general mental health in startups.

Disclosure — I know one of the Sanctus founders, George, who I met during the Ignite accelerator we were on last year. George was a programme director there, but left to concentrate on Sanctus.

4. Podcasts

Following signing up for Duuoo, I received an email from them about their podcast series, which gave me my very first “HOLY SHIT!” moment on this, ahem, “journey”. A real moment of realisation. In episode one, with Hampus Jakobsson, he says in literally the first two minutes:

“When you’re growing..[….]..the biggest challenge is getting the founders to understand that the team is the product”.

Of course! How many times have I heard that the team (and therefore execution) is more important than the idea. In fact, I’ve seen it with my own eyes a bunch of times. Great idea + crappy team = no chance of success.

So it stands to reason that you should (to an extent) develop your team like a product. Constantly be optimising them, making them better, happier and more effective.

There’s loads of great advice in this short podcast, including the creation of “How Do You Feel Dinners” at a previous startup he ran. And the second podcast with Gary Vaynerchuk made me realise that I’m *mad* to spend hours trying to please a crappy client who I’ll never make happy, and almost no time at all looking after my staff. I need to start thinking more macro than micro. The team is what drives the success.

5. Better communication

One thing I know I’m not great at is communicating. I think I’m a good listener, and (given time to consider everything) a good strategic thinker. But I don’t think I’m very good at getting complex ideas out of my head, and into simple, clear words for others to understand. Especially if I have to do it on the spot. This is massively exaggerated when dealing with staff members for whom English is not their native language. But I also need to be aware that as a startup founder I’ve been embedded in a certain way of thinking and “doing” that is second nature to me, but probably not to my employees. Unless they understand the bigger picture, end goal, and working methodology (and how they all interconnect), it’s no surprise if they get frustrated with things from time to time.

Startup founders by nature are probably comfortable with uncertainty, chaos, and reacting on-the-fly. There’s a very good chance that your staff aren’t. But you can make them more comfortable with these circumstances by communicating better, and preparing them for any surprises.

6. Employee engagement & onboarding

Following on from that, I’ve realised that it’s really important to set out “the bigger picture” if culture and strategy when bringing new staff members into the fold. What is the ultimate aim of the startup? What does success look like? What are the milestones? Next week? Next month? Next year? TEN YEARS?

I wrote a short strategy document a while back that I try to prod everyone into re-reading every month or so. It sets out what we’re trying to achieve on a long-term basis, and how that impacts our daily behaviours.

e.g. Long-term — get acquired by Facebook = short-term — make sure you tag Zuckerberg in all FB posts! (may not be real example).

There are a bunch of platforms that attempt to help with the induction process, and keep employees up to speed with the startups’s aims, as well as importantly keeping bosses up to speed with how the employees are feeling about their role.

I’ve not tried them all yet, as each requires a little time and commitment (and I want to be sure I’m choosing the right one before asking staff to spend time on it). But this is my current shortlist:

https://butterfly.ai/

https://www.tydy.co/

https://www.15five.com/

So, that’s where I am right now. Having never really had a “proper job”, I’ve never had the training or been on the personal development courses that I hear are pretty standard in a more corporate career. So after all this time I’m teaching myself.

I hope some of it is of use to you. And *please* post any advice, thoughts or feedback in the comments. I’d be very grateful.

Neil is the CEO and co-founder of RampTshirts.com, the world’s fastest, smartest t-shirt ordering site for teams and events.