9 Leadership mistakes I'm trying to not make again

I was  in San Francisco on Martin Luther King day this year for a week of training, we spoke at length about the late Dr. King and how he embodied so many of the qualities we expect from exceptional leaders. This conversation inspired me to reflect on how I can improve as a leader and the many mistakes I've made (and continue to make) getting to where I am today.

Great leaders come in all shapes and sizes from all facets of life, entrepreneurs, sports coaches, politicians and parents all need to be leaders.

Being a leader doesn’t mean that you're responsible for people, it means that you’re able to help people understand and believe in your vision and that they will work with you to achieve your mutual goals. For the sake of simplicity, I will often refer to a team and work environment in this post, but these points can be used with your colleagues, friends, family or anyone that you want to inspire and lead.

Here are 9 leadership mistakes I’ve made and learned from the hard way:

1. Focusing on negatives – Don’t get me wrong, I’m not suggesting that we should all skip around blinkered avoiding our problems, it is vitally important as a leader that you are able to identify challenges and tackle them head on. When it comes to your team, however, you should be able to list the things that each of them is exceptional at, things that they do better than anyone else you know. These are the skills you should focus on, coach and celebrate daily – rather than chipping away at the long list of things someone needs to improve.

Think about your colleagues the way you would a sports team, each person has a set of skills that make them the right fit for the position they play. You shouldn’t train everyone to be average or good in all positions, those all-rounders rarely become champions, you want to scout potentially exceptional talent and train them to be world beaters for their role on the team.

2. Shutting down ideas - Remember that feeling at school when you asked a question and you were made to feel stupid because of it? It really sucks, don’t make people feel like that! 

If someone raises a point to you, asks a question or gives you a suggestion listen to them intently and ask questions until you have enough information to fully understand their viewpoint. Make sure that you thank them for the feedback and make a decision immediately or ask them to come back to you with more data (more on this later). 

Encouraging an open atmosphere of challenging conversations, idea-generation and empowerment will ensure that you’re getting very the most from your team’s unique talents. If you let them, your colleagues will help you avoid costly mistakes, reach your objectives faster and feel rewarded and empowered while doing it.

3. Taking on monkeys - Never respond to a request or inquiry with ‘let me get back to you’ or ‘give me some time to think about that’, unless you enjoy working long hours doing other people’s work - it's referred to as 'taking a monkey on your back'. Great leaders are able to delegate effectively and allow people to own their successes and failures.

You essentially have three options in that situation –

You have the data to make a decision now - make a decision!

You don’t have the data to make a decision - ask them to come back to you with what you need.

You can’t make the decision - don’t be embarrassed if something is beyond your realm of decision making, that’s why you have a team, point them in the direction of the person that can make that decision.

What’s that about monkeys? If you haven’t read the HBR article, read it.

4. Being unclear about expectations - It seems like a no-brainer, but how will people know what you expect from them if you have never made it clear? Targets and goals are easy, but day to day behaviors that are normal for you might be completely alien to others. Unless you have Mystic Meg on your team, you’d be smart to make your expectations very clear.

Ben Horowitz wrote this great guide to being a Good Product Manager vs Bad Product Manager. I find that making a list of behaviors that you expect to see from an unsuccessful, successful and highly successful person in that role is very useful. Now your team can focus on the things you care about in order to be highly successful and deprioritize other activities. This is not micromanagement, your team will really appreciate your clarity and be much more productive because of it.

Below is an example of what I share with new starters on my team:

5. Trying to please everybody – You’ve heard that making an omelet requires breaking eggs, right? You’re going to have to come to terms with having uncomfortable and challenging conversations as a leader, it is your responsibility to push your colleagues to their limits and they aren’t always going to love you for it.

Be consistently clear, fair and demanding with your team, let them know that you expect greatness from each of them. You want them to look back on you as the person who always got 110% from them and where they did their best work, not the David Brent-type who desperately tried to be their buddy.

6. Appearing unavailable – This one is really simple. If someone comes to your desk to ask a question, give them your full attention – if it’s not convenient at that moment book some time in the calendar. If you are sent an email or IM from a colleague always directly reply to it, no exceptions, even if it is to point them in the direction of the right person to contact. If you like to listen to music when you’re working, make sure you set aside time where you don’t have your headphones in so people can approach you.

You might have some conversations here and there that weren’t the most efficient use of your time, but they will be far outweighed by the productive conversations you will have, insights you’ll gather and constructive feedback you’ll receive.

7. Infrequently asking for feedback – Be honest, how often do you ask your colleagues for feedback? I don’t mean asking ‘So, what do you think?’ at the end of a presentation or meeting, how often do you dedicate time to asking, with genuine interest, ‘What are 3 things I can improve on?’, ‘How can I do this better next time?’ or ‘What are the things I need to stop/start doing?’. If you’re doing it at all, you’re already ahead of most people. Frequently asking for feedback will rapidly accelerate your development as a leader and allow you to crowdsource your growth.

Be consistent, dedicate some time each month to asking for feedback from your colleagues individually and as a team. Be open to the feedback at all times, try not to argue or become defensive – explain your actions only if you need to. Be appreciative, thank them for their feedback and let them know what you will be doing about it going forward.

8. Making ‘safe’ hires – Too often managers will, subconsciously or not, assess candidates on how much they match with their own views and interests. These managers will end up with a team of yes-people that never challenge them. Only hire people that will be significantly better than you in that role, and above the mean of their colleagues – they will bring a new dynamic to the team and you won’t be tempted to meddle in their work.

I always hope that each of my ‘new hires’ will eventually be so good that they uproot me from my job. In reality, that very rarely happens at a company, because the leader of exceptional people will improve at their rate. By building a team of, sometimes intimidatingly, exceptional people you will only ever be forced to grow and become a better leader – they will demand it from you.

9. Fearing failure – In the lobby of Facebook’s Dublin offices is a sign that reads ‘What would you do if you weren’t afraid?’. We’re all going to make the wrong call at some point, no matter the reliability of your data, expect and welcome those failures. A failure is going to be ok as long as you do 3 things:

- Test new initiatives, before fully rolling them out, to gather data and mitigate risk. Put everything through a beta phase. Ask Marks & Spencer about that million-pound website redesign they didn’t test.

- Fail fast. Don’t let your ego get the best of you! It is tough, but you need to admit you were wrong early, cut your losses and go back to the drawing board before real damage is done.

- Own your failures. Let everyone know that your initiative tanked, hold a retrospective and learn from it. Everyone makes mistakes, it is how you learn from them that demonstrates character.

I hope that these points inspire you to reflect on your own leadership strengths and weaknesses and that you feel more empowered to inspire and lead the people around you!

Let me know in the comments what your top leadership tips are.