My co-founder and I started our business in 2011 and in 2016 we raised enough money to suddenly have a room full of staff. As an introvert, this was a bit of a shock to the senses. I had to learn quickly how to lead a team effectively. I made plenty of mistakes and upskilled myself hugely. Based on this experience, and a recent mistake with a dud CEO hire, I wanted to share some points on what I think constitutes good leadership in a small tech start-up.
1. BUILD TRUST
To effectively motivate a team, you need to have their trust. They need to know you and you need to be honest and communicate well. But before any of that will happen, they need to like you. Regular team building fun and team lunches are important. Above this though is a personal connection with each and every staff member. I remember reading Dale Carnegie’s books as a kid, and really internalising his advice – if you want people to like you, take an interest in their interests and ask them about it. While your company is still under 20 people, you really need to get to know everyone. No favourites. Nobody you can’t stand sitting through a lunch next to and chatting with. The relationship goes both ways too – share a little of yourself, your personality, interests, weekend activities, and sometimes (careful now) vulnerabilities. You aren’t always Iron Man / Wonder Woman.
2. BE RESOURCEFUL
An integral part of being the man / woman in charge is realising the responsibility that has been entrusted in you. If you are going to have the chair (Star Trek reference), you need to fully grasp how important every minute of every hour of every day is. Your responsibility and effort does not stop at 17:00 each day, it is ongoing. You should be thinking, scheming, planning and dreaming about ways to grow the business at all times. You need to CREATE growth for the business, and not organic growth that is slow and steady, but BIG growth opportunities that demand a bit of boldness, a handful of hustle and a pinch of pavement pounding. You cannot simply respond to your email Inbox and call it a day.
If you are not a creative person, or don’t know how to Google things and upskill fast, you will not succeed in business development. Being in charge means constantly wondering just how far your unconscious incompetence goes and then doing something about it. It’s a lot like having a 24/7 existential crisis for several years. Grey hairs happen. You need to be able to realise you are lacking in xyz skills, jump onto Google and rapidly upskill by teaching yourself what to do. There is a certain dynamism here that accepts as central the fact that this is a growth role for you, not one of stagnation – not like anything you have run before. You don't have the answers. You have to find them.
3. GET STUCK IN
Leadership is a difficult balance of having to keep a lighthouse view on the stormy landscape around you, whilst also occasionally taking the lift down to ground floor and knowing how things work in the engine room. These are completely opposite mindsets or modes of thinking – big picture, long term and strategic vs problem-solving, immediate and practical – so keeping both in mind is definitely challenging.
In a larger organisation, it would make sense to setup Heads of Departments and hold them to account – leaving the details to them to figure out. The downside of this decentralised thinking is that your independence is undermined and you are unable to effectively pitch or pivot the business when you need to. You also don’t want to rope in the Department Heads to every meeting or pitch – they have work to do. Make an effort to get to penetrate deeper than the projections, as far as you can, and learn the details of how your company product works, your processes, customer support, marketing and sales.
Another angle to this which is important in a small team, is to demonstrate that you are not above anyone. When it comes down to birthdays, sometimes you buy the cake. When the cleaner doesn’t arrive, maybe you make the follow-up call. If there is a mug in the sink that isn’t clean – is it too much to soak a sponge? People appreciate the small gestures.
4. HAVE BACKUP PLANS
Unfortunately optimism doesn’t make partnerships work. You being excited doesn’t mean that all the myriad pieces that need to come together will do so favourably. Shit happens, and its kak. A big mistake to make as a small business is to put all your eggs in one basket. If the partnership you have worked so hard towards doesn’t deliver, you will be under the spotlight, and the cashflow which just disappeared could sink your business.
To prevent this, try to have more baskets – more opportunities running IN PARALLEL. Don’t get comfortable. Trust no promises. Know for sure that some opportunities will fail to close, fail to perform and fail to achieve expected timelines. Try to negotiate contracts that allow you to work with multiple similar partners with no competition clauses.
5. GET A SUPPORT STRATEGY
Think you got this? Think you are on top, riding the big wave, all looking good? That can change FAST. On this journey you will be slammed into pavement so hard, so often, that you will forget why you ever did this to yourself. You need to make sure you have a resilience strategy for handling the lows because they will come. It is unavoidable. You can’t do this alone – strong networks of communication are required to handle the stress and share your feelings with others. Things I have found useful are described in this post.
After you have finished crying, you will need to dry your tears. This is the time to call on people who you respect for advice. Whilst building your business and meeting a bunch of great people, start to befriend the ones who you get along with, who have “made it” and who are a few steps ahead of you in the path you want to follow. You can either setup an advisory board that meets regularly, or establish something less formal like an emergency WhatsApp group. In my business we did not setup a formalised advisory board and very much missed out on the opportunity for camaraderie on a lonely path, emotional support, problem-solving and creative ideas.
6. BE BOLD
You are running a team, ideally composed of excellent folks with great ideas. I remember being plunged into an unexpected personal crisis the first time I asked my team for ideas. I just asked for feedback one day on how to solve a problem, and got the worst response – valid feedback. The problem with the feedback is not the quality of ideas, but the conflicting nature of them, and the fact that resources are limited. I had to get comfortable with being decisive, whilst also leveraging the democracy of crowd-sourced good ideas.
This is the not-so-fun part of being a leader – you have to learn to say No to people with good ideas. Prepare yourself to say “Thanks but no”, “I don’t think that will work”, “We aren’t going to do that now” and be willing to do so politely and firmly, handling the disappointment that comes with turning down someone’s baby. It is hard when you share an open-plan office and stare at these people all day. They will remember when you said No, and when the thing you said Yes to didn’t work out.. Using data and objective reasons to choose some projects over others will help take the blame off you if you make the wrong choices.
7. BE A PESSIMIST SOMETIMES
In line with point number 3, sometimes things don’t work out as planned. In software engineering you have to imagine that everyone is a hacker out to crush you, everyone is running old browsers with multiple plugins over dial-up, everyone will hand in their tax return on the very last day (overloading your system), every small change could break everything and every server will crash – and plan accordingly.
In business, being a pessimist means always planning exhaustively for the death of any partnership at the contractual stage. Things may seem rosy in the beginning, and you might agree to lofty collaborations together, but in reality these don’t always pan out, so you need to very clearly spell out word-for-word the dramatic obituary in black and white. This can be hard to do at the start when all your energy and focus is on making things work. My more optimistic co-founder Marc would often rag on me for being so negative, but the contractual additions I made to legal agreements helped keep our partners in line and our business relationships and projections on track. Be nice in person, hard in writing.