Facilitating Retrospectives for Large Teams

Courtesy of ThoughtWorks

Recently I was asked to facilitate a retrospective for 26 people. Of course I said yes, but only afterwards did I begin to realise the challenge I faced. The reality is people work better in smaller groups, but sometimes you have to bring a large groups together. In this post I’d like to share how I ran this retrospective along with some of the learnings I gained. I hope you find it useful!

Things You’ll Need

  • A large room
  • Post its
  • Sharpies/Pens
  • 1-2 hours
  • Lots of wall space!


One of the biggest challenges in running a successful retrospective for a large team — that results in usable feedback — is to ensure that everyone is heard. As a facilitator it is our job to create an environment that encourages contribution, we achieve this by:

  • Creating a safe environment to speak.
  • Giving clarity to the plan and process.
  • Guiding discussions to keep them on track.

I have found that the retrospective introduction is key to establishing the right environment. It sets the tone for the rest of the session and provides the opportunity to cement your position as the facilitator.

I started the session by explaining my understanding of why we were all here and asking participants if this was their understanding as well. It’s important to get clarity on this early and surface disagreements if they exist, otherwise they will raise their heads at a less appropriate time.

In this session everyone agreed on the reason for being in the room so I walked people through the agenda for the session. I like to leave the agenda on the wall throughout the session with timings next to each agenda item, this means participants can facilitate and regulate their own discussion because they can see the plan and where we are.

Lastly I talked to the group about psychological safety. I reminded participants that not everyone is comfortable speaking in front of large groups and can sometimes be reluctant to share their opinion with others. It is our job to help make each other feel comfortable to express ourselves. I then read The Prime Directive to reiterate the intentions of everyone in the room and we conducted a Safety Check to test the comfort levels before continuing the retrospective.

Warm Up

The first exercise we did was an icebreaker, to get people into a collaborative mindset. I asked the retrospective participants to play the line up game. They had to arrange themselves in order of who was born farthest from our office in Soho, London. We had people all the way from Malaysia and Australia!

This exercise got people to get up, move around and talk to others they may not know well, subtly breaking the social or team groups that existed within the room. I also particularly like this exercise as it demonstrates the diversity of the team, providing a very visual way to explain how different backgrounds bring great team value but also affect our ways of communicating and interacting.

Getting Input

Now we step into the retrospective session itself. It was important to find a format for this that enabled everyone to contribute. I was especially mindful of making sure that the quiet voices would be heard while at the same time encouraging people to go beyond their comfort zones – ensuring that we got meaningful feedback.

To achieve this I decided to run the first part of the session with the whole group, but asking them to work individually. I set up four stations around the room, each with a different title – Liked, Learned, Lacked and Longed for. I asked participants to take ten minutes to write their own thoughts on post it’s and put them up on the relevant section. I encouraged people to spend the first five minutes writing, then walk around, stick their post it’s up and start to read what others had put to prompt new ideas.

Group in Groups

Once we had input from everyone, we needed to refine the content on the walls. I split people into four mini teams, one per section, and asked them to put all the post it’s that referred to the same point together to form a topic. When they did this, I asked them to summarise the topic on a large post it note and place it over the top to make it clearer for those reading.

By separating into groups at this stage it made it quicker to refine the content and reduced the stress on me as a facilitator.

Read & Vote

Once the topic grouping was complete I asked each individual to put a dot on the topic that they felt was most important to them on the board they were at. We then rotated the mini teams to the next section and asked them to do the same, giving them the opportunity to read what their colleagues had put in these sections too. We did this for each section until the mini teams were back at the section they started at.

Once all the teams had voted, I went around each team and asked them to present the topics back to the entire group.

Rather than discussing each of the topics in depth, I asked people to raise their hand if they needed clarification on any of the topics or had any questions. The general rule was that the person clarifying would just explain the intent of the note in a couple of lines and we would avoid any lengthy discussions at that time.

Get to Action

Through the exercises so far we had identified several topics that people wished existed or were improved. We took the top four voted topics and distributed one to each of the mini teams to create possible ways to solve the problems. I gave each team a hypothesis template and gave them ten minuites to fill in the gaps in the statement below:

We believe that….
will result in….
and we will know we are successful when….

The hypothesis template structured the ideas teams came up with, drove them to identify exactly what their idea is aiming to change and encouraged them to provide a measurable way to know when the change has been made.

I then had the mini teams present their hypothesis back to the wider group and we agreed owners for each of the hypothesis. The aim was to leave the retrospective knowing what they would try to improve and review progress against these hypothesis in a month.

Running a retrospective with a large team is challenging. However, with good preparation they can be used effectively for gathering feedback, building team connection and making meaningful change. I hope this article may help you planning your own retrospectives.

The Rise of Open Startups

Can you guess the monthly revenue run rate for the online publishing platform, Ghost?

The answer is $143,931. I’d ask if you guessed right, but if I’m honest you didn’t need to guess, you could have just visited Ghost’s website to find out!

Ghost is one of a growing number of startups that are operating transparently — sharing company data that previously would have been limited to employees and investors. They refer to themselves as an Open Startup, but what does this mean and why would you run a company publicly?

What’s An Open Startup

An open startup is a company that has chosen to publicly share metrics about their company. Normally they share revenue, users, and traffic numbers but in some cases they will even share, logs and dashboards too.

The trend for transparency and openness appears to have been started by Buffer, but now has been adopted by several other companies like ConvertKitGhost and Nomad List.

Ghost’s Annual Run Rate

Why Run An Open Startup

Marketing: It’s been demonstrated by NomadList and Baremetrics that publicly sharing statistics can be used for promotion and to increase traffic. Equally sharing a growing user base is ideal social proof for potential customers. That said, being open can work both ways. Low user numbers or revenue could have the complete opposite effect and deter customers from purchasing.

Feedback: Sharing development progress and roadmaps is an excellent way to gain real-time feedback from existing users and potential customers. Monzo has done this very effectively with its public roadmap.

Education: Being transparent about how a company is gaining customers, building a product and making money provides an excellent opportunity to dispel the myths around startups for customers, investors and founders. More public information can also help the industry progress, encouraging others to launch independent companies.

Whether you agree with the Open Startup movement or not, it’s undeniably intriguing to be able to see how companies like Ghost are growing. 

I believe opening information previously restricted to a privileged few plays a part in democratising the startup world. I hope to see more companies open their data as I’m sure it can benefit us all.

How Jurgen Klopp Transformed Liverpool’s Culture

Image from Sky Sports

I’ve long been fascinated by the parallels between sport and business, especially how activities off the field can dramatically impact the results on it. Over the last few years, I’ve been watching the change at Liverpool Football Club with interest. It’s not so much the success that intrigues me but more the change in culture that began with the arrival of manager Jurgen Klopp.

Over the weekend, I listened to a great analysis of Klopp’s leadership on the podcast Eat, Sleep, Work, Repeat. After listening to the show I think there are two critical elements that have supported change at Liverpool and I want to share these with you today.


When he joined Liverpool, Klopp made the point of learning the names of all eighty employees at Melwood the clubs training ground. He lined them all up in the dining hall and introduced them to the players. Klopp explained to the whole group that they all had a responsibility to help each other achieve their best.

Creating a sense of inclusivity and family is critical to the Klopp approach. He works hard to make the players and staff feel valued, which creates inclusive energy that can sustainably engage people.

A study found that 74% of engaged employees believed senior leaders had a sincere interest in their well-being. While in a similar sample of disengaged employees, only 18% felt their managers genuinely cared about their well-being. The study suggests that leaders can increase employee engagement by expressing emotion and creating bonds that unlock better performance in colleagues.

This raises the question of whether engagement is Klopp’s secret weapon to delivering better results on the pitch?

In an analysis of 50 global companies, consulting firm Towers Watson found that companies with low engagement scores had an average profit margin of just under 10 percent. But those firms with high engagement had a slightly higher margin of 14 percent. The superstar firms with the highest engagement scores had an average profit margin of 27 percent.

I think the same is happening at Liverpool. By Klopp expressing interest in employees, he is dragging up their engagement and connection to the cause, giving everyone a sense of shared purpose.

Psychological Safety

We’ve seen how creating connection, engagement and shared purpose can lead to greater success, but this benefit could be quickly eroded without creating psychological safety.

Psychological safety is a shared belief that the team is safe for interpersonal risk-taking. It’s characterised by mutual honesty, honesty of the team with the boss and the boss with the team.

Klopp creates safety by encouraging his team to take chances. He would tell his players he would rather see them shoot and miss, than not try at all. He famously will not criticise technical errors and instead consoles and then encourages players when these are made. Ultimately psychological safety is about letting players know they won’t be blamed for giving everything they’ve got.

Klopp also reinforces psychological safety by how he deals with mistakes. In 2018 Liverpool were beaten 3-1 in the Champions League final after two shocking mistakes made by Liverpool goalkeeper Loris Karius. However, in an interview after the game, Klopp never blamed the goalkeeper. In contrast he complimented him, saying he was a fantastic individual who would recognise the errors.

Although Karius left Liverpool shortly afterward, the way Klopp treated him as a person is to be admired. It demonstrated to others they would always be respected and treated fairly at Liverpool.

If we want our teams to be creative, we can’t punish them for mistakes. Klopp goes out of his way to show that no one will pay the price for making mistakes.

It will be interesting to see if Liverpool can repeat their successes in the coming seasons. Building a self-sustaining organisational culture is a challenge that has eclipsed all but the best leaders. It will be interesting to see if Klopp can prevent the burnout seen at other clubs who have gone through a shift in culture.

Whatever happens in the future, I think Klopp’s success is best measured not by football results but how he is seen as a human. I will leave you with this quote from defender Virgil van Dijk which I think encapsulates Klopp’s success best.

“He is a fantastic manager first and foremost, but he is also a fantastic human being as well. How he handles us as players at the games and outside the games is outstanding. It’s a pleasure to work with him and with all the staff that work at Melwood. It’s an amazing environment to be in. I’m very proud and very glad that he wanted me to play at this beautiful club.”

Put Your Money Where Your Mouth Is

Between September 20 and 27, a record 7.6 million people took to the streets and went on strike for climate action. It was the most significant climate mobilisation in history involving 186 countries, 73 trade unions and 3024 businesses.

It’s these businesses that I want to focus on in this post. It was amazing to see companies like Ben & Jerrys, Patagonia and others closing their offices and stores around the world, to support their employees in striking. It was good to see them putting their money where their mouth was and taking a short term financial hit, for doing what was right.

That said there were a lot of companies that didn’t do the same. These companies are keen to talk about climate action and social responsibility in their marketing, and many even paid lip service to how they supported global climate strikes. But they continue to operate their businesses as usual, not willing to bear the financial cost of practising what they preach.

While I do care about the issue of climate change, I am not arguing in this piece that you or your company should care as well. However, I find it highly hypocritical that companies who advocate for social change in their mission statements and marketing activities refuse to make the difficult decisions required to make the change they claim to desire.

For many of these companies, doing social good is a significant component of their brands. It helps them sell their products and recruit talented employees. They reap the financial rewards that come with standing for more than just economic enrichment. Isn’t it time they also put their money where their mouth is and invest in the change they claim to want?

Taking Time to Reflect

Do you ever feel you need to pause and reflect?

In a world where we are always asking ourselves “what’s next?” I think it can be equally, if not more, important to look back and ask, “how did that go?”.

At work, we run retrospective sessions regularly with our teams to allow us to reflect on the previous week. We share what went well and how we could improve. I find this such a powerful practice, but it’s only recently I’ve begun to embrace retrospectives more personally.

It started with journaling more regularly. I write about experiences or situations I found challenging, and this has helped me understand myself better. Now, I want to extend the retrospective practice to reflect on the activities I do such as, work, fitness and now blogging.

Which brings me to the purpose of this post. I’ve decided to take a two-week break from writing here. Mainly because I’m taking an overdue holiday, but also to reflect on the experience of writing.

I think these moments to pause for reflection are vital to improving. I’m looking forward to looking back and how it will inform what comes next!

5 Lessons I Learnt From My Failed Startup

BitMate was a web application that helped developers start new projects faster. Was, is the keyword in this sentence. I founded BitMate in August 2016, but nine months later, I was closing it down.

Here are the mistakes I made and the lessons I learned through my experience as a founder. If you are thinking about starting a company or at the beginning of your journey, I hope this post helps you avoid making the same mistakes I did.

Start for the Right Reasons

In 2016 I wasn’t happy. I was working with a great group of people, but I found my work uninspiring and unfulfilling. I was frustrated at my lack of opportunities, and I was facing challenges in my relationships outside work too. I felt like I needed a clean break, a new challenge and starting a company in a new country seemed like it would be the answer.

I took the leap, left my job, moved myself to New York and started BitMate. Those first few months were exciting and full of promise as I set out to fix all the problems I was facing in my life with one cleverly designed solution. But as the reality of my new challenges began to sink in, my problems began to magnify.

Looking back on that time now, I realise I was nieve. I wasn’t passionate about the reasons for starting BitMate or the problems my potential customers had. I was looking for a way out of the challenges in my life at the time.

Moral of the Story: Starting a company is hard, and the chances of failure are high. It’s unlikely it’s going to pay off in the short term, so I think it’s vital to fall in love with the process, not the reward. If you love the process, the rewards will probably look after themselves.

Don’t Assume Your Customers Are like You

The idea for BitMate came from my own experiences, working as a developer building proof of concept applications to help companies validate product ideas. I needed to start projects quickly and didn’t want to build similar functionality from scratch every time.

While working on projects, I started writing scripts to generate code and speed up my work. Gradually these scripts got more and more complex until I could build the base framework for new projects in seconds.

I showed what I had built to some of my teammates and got some positive feedback. I thought what I had created could help other developers reduce their workload as I assumed they experienced the same problems as me. That turned out to be a big mistake!

Moral of the story: Don’t assume that your problems are the same as other peoples. Even if you find a few others with the same, that doesn’t mean there are enough people with that problem to start a business. I realised too late that most developers didn’t start new projects as often as I did so didn’t need BitMate.

Show Customers the Product, Quickly

Before starting BitMate, I had read The Lean Startup. I knew I needed to get my product in front of customers quickly so I could get their feedback. But when it came down to it, I was worried about showing potential customers a lousy product. I spent four months working on the product alone. I didn’t show anyone what I was building, and the scope kept creeping.

I know now that I was scared of negative feedback on my creation. It was more comfortable to build another feature, or improve the design than to find potential customers and risk them not liking my product.

The more I invested, the worse this problem got. I was committing the Sunk Cost Fallacy, avoiding showing people the product for fear I had wasted time, money and effort. I continued to invest with the crazy belief that the more effort I put in, the more likely customers would like it.

Moral of the story: Put your solution in the hands of potential customers early. I mean, really early. Ideally, before you’ve written any code, or invested any money. Talk to them about the solution, build a paper prototype, or try to sell your solution before it exists. Do anything you can to get validation before investing too much time and money.

Consider How the Product Scales

I never got the opportunity to see if BitMate would scale to thousands of customers, but I know it wouldn’t have been possible.

I thought BitMate’s customers had the same problems as me, which meant enabling them to start projects that combined lots of different options. However, when I finally began to talk to potential customers, I realised people wanted even more combinations than I thought. With every extra option, the complexity of the product grew exponentially.

By the time I closed BitMate, our product had become hugely complicated. We still only asked eight questions to customers when we built an application, but each question came with multiple choices. It meant BitMate could generate over 1,600 different variations and each of these had to be tested to ensure they worked every time we changed anything! At this point, adding one more question would have increased the possible variations exponentially to over 3,000!

BitMate could never have been a successful and sustainable product at scale. It only took simple maths to realise we would have drowned in technical complexity.

Moral of the story: Start with the end in mind. Begin by considering what success at scale means for you. It doesn’t have to be a billion-dollar exit or millions of customers. Instead, it might be a reliable income and more time to spend with your family. Either way, work out how much revenue and how many customers you think you need at scale. Consider what you’re company would look like, how many people work there, what the product would look like, and what you’re role will be at the company.

Building a good picture of where you want to go allows you to work backwards to avoid creating a company that cannot reach those goals or takes you somewhere you never wanted to be.

Build a Support Network

When I started BitMate, I turned my life upside down. I left my job, moved country and started a technical and business challenge more significant than I had attempted before. I had great support from my partner, family and friends, but if I’m honest, I was out of my depth.

As the months wore on the loneliness of my situation became very real. I was working alone, harder than I had before, but I wasn’t achieving what I had hoped. When I did see friends, I put on a brave face. I would say I was almost there, success was just around the corner, but that couldn’t have been further from the truth.

As this cycle continued, I could feel the effects on my mental and physical health. I was frustrated at myself for not being able to find a way to turn the impending failure into a success, and this undoubtedly put a strain on my relationships.

It took me a long time to realise that closing BitMate wasn’t a personal failure I couldn’t recover from but an opportunity to put my energy into something else. Since then, I have spoken to many other entrepreneurs who have experienced similar challenges, if only I could have spoken to them during the struggle.

Moral of the story: Starting a company can be a lonely experience. You will go through tough times and experience many failures. Family and friends can provide excellent support but be careful not to lean on them too much. They don’t want to live your startup journey aswell! Instead, try to build a support network of other entrepreneurs who understand what you’re going through. Attend meetups, go to conferences, and read about others experiences and consider getting a co-founder.

Lastly, remember to keep perspective. Struggling and failing can be emotionally stressful, but there is no shame in it. It’s essential to look after your physical and mental health through the journey so, even if this startup fails, you are ready for your next experience!

Starting a company is hard; eight out of ten new businesses fail in the first 18 months (I managed it in nine months!). Although we all want our ventures to be a success, I think you learn more from the failures than you do from the successes.

I have no regrets from my time running BitMate. I learned more about myself, how to create a product, and how to run a company in those nine short months than I had in the previous few years.

I hope by sharing my experiences, I don’t discourage you from starting you’re own company, but instead, inspire you. Just by reading this, you are better equipped to start than I was as you can try and avoid the mistakes I already made!

And even if you do start and fail, don’t be put you off. Welcome the experience because it’s setting you up with deeper insight, more conviction and better odds for the success next time.

Good Luck! 

The 5 Stages of Productivity

Productivity is a measure of output over time. All other things being equal, the more you produce per hour, the more productive you are. There are lots of ways to increase productivity, but I believe all increases in productivity fall into one of these five stages.

The First Stage: This is the simplest, get better at the task you have to do. Work harder and develop your skills.

The Second Stage: Find people who are cheaper than you to do tasks for you. People working together should be able to get more done, faster.

The Third Stage: Invest in tools that can boost the team’s output. For example, buying a digger for a team that previously dug trenches with shovels would significantly increase their output.

The Fourth Stage: Invent in new technology. Creating new technological innovations is how considerable leaps in productivity occur. Often these leaps enable huge savings or massive increases in customer value creation.

The Fifth Stage: This is a step that most of us never reach: At this stage, you need to figure out better things to work on. At this point, you can’t achieve more by working harder, smarter or finding more people. You can no longer react to demands. Now you must go your own way.

The fifth step is where the real productivity improvements occur. Saying no to somebody else’s demands and finding another way to achieve the goal. This is what separates great organisations from good ones, extraordinary people from frustrated ones.