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The Complete Guide to Establishing a Collaborative Company Culture

Future-proof your startup by taking it from a “cult of personality” to the next level by using this proven step-by-step method

Claire Millard
Nov 27, 2018 · 17 min read
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Photo credit: Vladimir Kudinov on Unsplash

a leadership coach, I work with driven, high-performing startup founders and entrepreneurs who are overwhelmingly impressive, but have reached a plateau in their careers and need to grow.

My primary work is to help these great entrepreneurs — who typically have very strong personalities — convert their personal success story into an enterprise-wide narrative which engages every employee. Done right, this creates the roots of a business which empowers and enthuses its team, and creates a virtuous circle as the organization grows.

As a startup founder or entrepreneur yourself, you’re growing your business, and will move through several stages of the enterprise lifecycle as you build your team and establish yourself.

If you get caught up in the ‘me’ of the investment round and forget the importance of investing in your core team, your startup can end up feeling like a personality cult built around one or two truly inspirational individuals. The rest of the team are left fading into the background, slowly losing their passion, and sowing the seeds of a dysfunctional organization culture which will come back to haunt you.

As a startup founder, it can be tricky to find the time and focus to think proactively with your team about the culture of your business. Investors famously bet on jockeys, not horses — so they’re often interested first and foremost in whether you, as an entrepreneur, are credible, capable and inspiring. It’s natural that while you’re establishing yourself and securing investment, you’ll be talking a lot about you — and less about the team you have or hope to build.

However, once you have a business up and running, what made you successful before could actually hold you back.

The fact is that, as soon as you have a team, a working culture has started to form. The language you all use with each other, the practical day-to-day ways of working you sign up to, the atmosphere in your office, or the tone of your meetings all contribute to the culture and internal brand.

One way I help entrepreneurs future-proof their business is by showing them how to build a strong internal brand and company culture.

Telling people what the culture is — or what it should be — doesn’t work.

Culture is largely made up between the lines, and grows organically. However, acknowledging with your team that you’re all on a journey together, and that you can choose the environment you want to build together, helps harness the power of the group to build a healthy culture — one that allows talent to flourish.

Running an active company culture-setting session with your team is a great way to empower everyone to own and grow the right culture for your growing business.

What follows is the methodology I use with my clients, which you can use to run a complete culture-defining session to get clarity and buy-in from the entire team.

How to run your own culture-setting session

This article will run through a suggested outline — including some exercises, prompts and ideas — for a culture-setting session. If you’re planning on running a group discussion like this, there will be some practical planning you need to do to make sure you can pull it off. For example, if you’re running a face-to-face session, a great way to stimulate discussion is to have everyone answer certain questions or prompts on a Post-It note, and then fix the Post-It notes to a page of flip chart shared among the group. It is old school, for sure, but it means that the facilitator can pull together notes which say similar things, and visually share themes and ideas as they emerge.

The exact details of your session will depend on the sort of team you have — whether it’s small or large, remote or in one building, for example. The best idea is to read through the guided steps here and then set about tailoring the session for your needs, using these ideas.

1. Define your team ‘units’

In some businesses, you can do this as a meeting with the entire team —for example, if you’re a team of 5–10 people, or a group of co-founders. However, in larger businesses, you might need to work with smaller groups first. For example, have your developers work through the session together, your sales and marketing team work through their own sessions, and so forth. Then, have representatives of each group come together to compare and align what they came up with.

The key is to make sure that everyone — including junior members of staff, admin associates, and even remote workers — has a voice in these sessions. If you’re not all based in the same location, you can run these sessions using whichever screen-sharing app you like best.

2. Set up great facilitation

Throughout the session (or sessions, if you have a large team), you’ll work through a group discussion. This should be facilitated by one person to make sure the event is smooth and slick.

A facilitator has a pretty tough task — they make sure everyone in the meeting is heard, they manage the pace of the conversation so that the group meets its objectives and stays on schedule, and they make sure crucial details of the meeting are captured and recorded.

A good facilitator must keep a neutral stance on the topics under discussion. If you yourself have a very strong personal view, you’ll have a bias — conscious or not — and it’s going to be hard to make sure everyone else is heard equally.

Who should be your facilitator for this meeting? An external facilitator is ideal, but if that’s not possible, choose a facilitator in advance from within your team. This doesn’t have to be the boss. In fact, in many situations, having the boss as a facilitator can be intimidating. Choose someone who is confident and articulate, but not necessarily among the most senior faces. Bring them on board to help you with the rest of this plan.

The facilitator can also help you decide on the actual space that works for hosting the meeting. That’s typically a conference room if you’re hosting a face-to-face meeting, or talking through the right approach if you have to do this remotely.

You’ll also want to create an agenda for the session: an outline of steps the facilitator will help the group through.

3. Announcing and marketing the session to your team

This culture setting session should be fun, high energy, and creative. However, some team members may be more reticent with their ideas, or simply haven’t done something like this before. Sharing your plan in advance ensures that they’re prepared and comfortable walking into the room to share their ideas.

You’ll also need to create an invite to your team which really inspires them, and has them buzzing before the event. You could try something like this:

“I know you, like me, are a proud member of this team. We are all passionate about what we do, and want to bring our best selves to work each and every day. That’s why I’m so excited to invite you to our inaugural culture-setting session. I know you’ll have questions about what we are planning — so there are some pointers below, and my door is open if you want to catch up or ask anything else!

What is a culture setting session?

Good question. A culture setting session is an opportunity for our entire team to get together and really dive into what we want our company culture to be — how we want the business to feel. We will then start to shape some action steps to help move us towards this.

Why do we need to do this?

We are growing as a business, and it’s exciting to be doing more new stuff, faster than ever. But it’s really important to me — to all of us — that we never lose sight of why we are all here and why we love the team we are in. This session is about working together as a team to define the way we want our business to look — and more importantly, feel — in the next year, 5 years, 10 years.

What exactly is company culture anyway?

Even better question. Company culture is how your workplace and team feels. Think of the words you’d use to describe your job, if you were asked at a dinner party. Or if your aunt was to call and quiz you on how work is going. Company culture is how you actually feel about your work — not how we tell you you ought to feel! It’s the informal, the emotional, the invisible glue that holds a team together.

What can I do to prepare in advance?

You don’t have to do anything formal to prepare for this session — but it’s not meant to be a big surprise either! We will work through a set of questions, which basically look at how we want our team to look and feel in future, how we think we are currently doing against that benchmark, and how we can make positive steps towards our aim. Brainstorming descriptions about how you want to feel walking into work on a random Monday morning a year from now is a great preparation — do you want to feel you have creative freedom, a supportive manager, and flexibility to tackle projects you love, for example?

Details of the session follow — I’m looking forward to sharing this important event with you all, and always here if you want to ask questions!”

You’ll want to keep an ear to the ground to see how this announcement lands.

One client I worked with who ran this session — let’s call her Laura — came back to talk her approach through with me. She noticed that some of the newer recruits on her team didn’t seem to be enthusiastic about the meeting. She read this as disengagement, and was concerned that these new team members didn’t care about the session, or the results of it.

We talked through some possible approaches, and Laura decided to talk individually, in a relatively casual environment, with team members to explore what she was noticing. It was quickly apparent that the last couple of team members to join the business didn’t feel that their say was as ‘worthwhile’ as that of more established colleagues, or of the cofounders.

This insight allowed Laura to reassure them that their voices were absolutely welcomed, and that they were even able to offer a unique and valuable view of the team from an ‘outsider’ perspective. She challenged them to use their newness to their advantage, commenting on their observations as recent joiners, and sharing what they see the team already doing well. Laura was also able to warn the facilitator of these concerns so he was able to keep these colleagues fully involved and engaged throughout the meeting.

4. Opening the meeting

The day of your culture-setting session arrives, and it’s time to get started. Consider how people might be feeling right now. For many people, this might be a nerve-wracking, and you want them to put people at ease. Have the facilitator outline the goals and agenda of the session. That agenda should be visibly posted somewhere for the group to follow.

Your facilitator can open by saying something like this:

“Welcome to our culture-setting session! We are all here today to talk through some of the most important questions we have as a business, and to help describe and develop the company culture we want to work in. Everyone’s view matters, and so we will make sure that the whole team has a say, and can share ideas and concerns. We are going to talk through 3 key questions:

What do we want our company culture to look like?

How are we doing against that measure right now?

What actions can we agree today to move toward the company culture we all aspire to?

The objective of the meeting is to start to paint a picture of the workplace we want to be in, in 12 months, or maybe 5 years — and while our business will doubtless be growing and changing. We are working to define the DNA of the company, and by doing so we can help make sure we preserve, and evolve it. My role as facilitator is to make sure everyone is heard, and our ideas are captured. By the end of the meeting we want to have some agreement on actions we can take to begin building the culture we want, and some ideas about taking the work to the next level.”

Hopefully your team is starting to move from nervous to excited by this stage. However, it’s still worth running an ice breaker or two to get everyone’s thoughts flowing and engaged. My favorite opening icebreaker is ‘left luggage’ — simply give everyone a Post-It note or two, and ask them to write down all the random things that are playing on their minds: that project that needs finishing, what to do for dinner, whether the kids did their homework yet, etc. Stick these notes on the back of the door, and tell everyone they can collect them as they leave. This is a remarkably cathartic and soothing way to start an important session!

It’s often a smart idea to arrange to have the ice breakers run by someone other than the main facilitator. This means that the facilitator has one less thing to worry about, and it also brings more people into the active running of the session.

Finally, as part of this opening session, you should set out some ground rules for the meeting. You want to generate these organically — ask the team what they believe the guidelines for a healthy meeting should be. The sorts of things you might get back as ideas include:

  • Everyone’s views are welcome — we will all work to involve the entire team in the conversation, by asking genuine questions with a curious mind.
  • If we need to break, we call it — better the take a quick walk then mentally leave the meeting.
  • We will criticize ideas, if we need to — not people.
  • Everyone will join the discussion with the intention of hearing and understanding opposing views.
  • If we agree that a disagreement can not be resolved or pursued any further today, we will park it, clear our minds, and move onto the next point. Parked items will be picked up later by those involved.
  • We are aiming to create action, and jointly plan next steps that we all own.

5. Question 1: What do we want our culture to look like?

This should be fun and high energy — it’s a ‘no wrong answers’ kind of environment, and we want everyone to share their views.

You’ll be brainstorming people’s ideas about what your culture should look like. Using Post-It notes is a great way to do this if you’re meeting in person. Different teams respond differently to this exercise, so you’ll need to tailor it your work group — here are a few starting questions to get the ideas flowing:

  • In 12 months time, how do you want to feel as you’re walking through the door on a random Monday morning?
  • What words do you want to use when the person next to you at dinner asks what you think of your workplace?
  • Picture yourself a year from now. How do you and your team set goals? How do you solve problems? How do you know you’re doing a good job? What happens when things go wrong?

You can ask individuals consider their own ideas for a short quiet time — ten minutes is usually enough. Then, you could have pairs discuss their thoughts, before sharing with the group — or skip right to a group discussion if you’d rather.

Another facilitation method you can implement is the “Round Robin”. To conduct a Round Robin, you ask each person in the room for their quick input, one after another, and continue making rounds until everyone passes. It’s a stellar facilitation method to ensure that everyone is heard—not just those with the loudest voices.

The facilitator is working to pull out themes — does everyone agree that the workplace should be somewhere we can be free to offer and receive feedback, for example? Is everyone leaning towards an environment which allows individuals to choose the projects they pick up, or where public recognition for good work is just normal? Oftentimes, people will say similar things in slightly different words, and a great facilitator will highlight and capture these shared ideas.

One of my clients who was running this session with a fairly large group shared with me that his external facilitator helped moving the conversation, along with lots of re-framing of points to help everyone understand and consider them. One active listening technique the facilitator used was to pick up an idea shared by a group member and say, “so, what I think you’re saying is…” then summarizing the point, confirming his understanding, and writing it down on a shared noticeboard. He then asked for others to build on the idea, or share their own related view.

This created space for other team members to add their ideas, so the resulting point on the board was not the product of one team member, but a view genuinely sourced from the entire group. In the post-meeting review group, the team noticed that this approach made people feel comfortable and collaborative, rather than competing to make sure ‘their’ views made the final cut. It’s definitely a technique I’ll use next time I facilitate this meeting!

Wrap up this slice of the session by saying something like, “Fantastic! We have now started to create our blueprint for how we want to work, how we want the team to feel in years to come. These are the ideals and standards we will aim for, and now we’ll talk about how!”

6. Question 2: Where are we now against these benchmarks?

You’ll probably want to take a break after question one, mentioning as you do that this will be the next question you’ll all tackle together. In it, you discuss how you stack up next to the ideal components of your company culture captured in question one.

This session can prove controversial if there are disagreements, or the team is not entirely engaged at the moment. However, it is important to complete — and airing views in a constructive way really does bring the team together.

Here, too, your facilitator can give people some alone time to ponder the question first, before sharing with the group. The facilitator should work through the set of themes — your ideals — that you have created in question 1, and get some frank views on how you’re measuring up.

You could do this using free discussion, or steer the conversation by asking people to rate your current level against different ideals. Simply pick one out — let’s say, you’ve agreed that a cultural value should be to have a creative workplace — and have everyone hold up a rating by showing 1–5 fingers. The facilitator takes a rough average, and you have a score. If you’re a 4 or 5 out of 5, well done — but if it’s a low mark, this might be one of the items to tackle in the next step. Go through the list of what you want in your culture from question 1 and rank how well you currently do in meeting each.

Dealing with disagreement as a facilitator

If you’ve ever been a facilitator at any sort of meeting, the chances are you’ve had to deal with some sort of disagreement or conflict — I know I have! It’s uncomfortable — but necessary, and it does actually help the group to verbalize issues from time to time.

Question 2 is where most teams start to encounter disagreement among team members.

How best to deal with conflict as a facilitator depends a little bit on what you’re seeing. If someone is making a personal attack, it’s important to intervene quickly. Remind the group of the ground rules, and highlight the wording which was inappropriate.

It’s also useful to spot and stop side conversations as soon as you can, as these are distracting and contribute to a negative atmosphere. You can do this in a really cheerful way — by asking those involved in a side conversation their opinion on the main topic of discussion.

In general, having some disagreement within the team is neither unusual nor too much of an issue. As the facilitator you can try to reframe the points which are causing argument, to see if others can understand — even if not agree — with them. Recognizing and capturing conflicting views, and then parking them to be handled later, is sometimes the best you can achieve. If you can get to a point where all authentic views are understood respectfully, you’ve done a great job — even if agreement is still impossible!

7. Agreeing on action items

This step is crucial, because a session which turns into just “talking shop” can be more damaging than motivational. You need to set some positive actions that can help move the company culture where you want it.

Depending on how the previous steps have gone, you might have a really obvious project to tackle this stage. Perhaps there are one or two major areas that you want to focus the discussion on improving. If not, turn your attention to how you strengthen elements of the culture you already do well.

How can you future-proof these important features of your business — for example, how do your new team members know that these are things that matter to you?

Here are some examples of action items which you and your team might consider:

  • Create an induction plan for new employees, which features information about your company culture.
  • Work on creating a core values statement.
  • Create an employee reward and recognition process that supports the culture you are seeking to create.
  • Create a regular time for the team to revisit the cultural values agreed upon, and check in with progress.

Each action item should have a person assigned who is responsible for ensuring that it is done. That person might delegate, create a working team, or do it themselves—but in all cases, they are responsible for seeing it through.

Your list of action items should address any specific needs which came up — for example, if one of the cultural values identified is that employees want to continue to learn and develop at a rapid pace, then creating opportunities for them to take on new projects, study online courses related to their discipline, or buddy up with someone else who has skills they want can all be effective tools.

Laura — the previous client who I mentioned above — was able to pick up on her new recruits’ concerns, and to use their position as recent joiners, to involve them in creating a formalized induction plan for the next set of new team members coming on board. By teaming up some newer colleagues with some that were more experienced, the resulting induction plan was solid, and the whole team got to know each other better along the way.

8. Wrap up and follow up

Hopefully your culture-setting session has felt like a positive experience for the team.

It’s important to leave the opportunity for individuals to ask more questions, or say things they might not have been confident to say in the moment. As a leader or facilitator, part of your wrap up of the session can be to offer follow-up time for anyone who wants it.

Be sure to thank everyone for their contribution — chances are this was a new experience for some members of the team, and might have left them feeling a little exposed.

It’s also a smart idea to send out a summary of the action steps that were committed to, and to agree how you’ll keep this work alive. Perhaps can ask someone to schedule a follow to see how the commitments are shaping up. Or, you could host an engagement survey in a month or two to see how people are now feeling against the cultural measures you’ve set yourself.

Building a business is an exciting experience. If you’re an emerging leader with a startup or medium-sized business, you have a great opportunity to create a working experience that helps people to flourish. It can feel like a big responsibility — you have to worry not only about running your business and looking after your team’s needs, but you’re also working to make sure the workplace environment is engaging, motivational and encourages open and collaborative work.

But you’re not alone. By using a culture-setting session like this to openly discuss the cultural and environmental things which will help your team to grow, you’re empowering them to take some control themselves. Get everyone pulling in the same direction, and it creates a virtuous circle in which responsibility on you starts to lift as the whole team can drive the cultural values you’ve agreed.

Better Humans

Better Humans is a collection of the world's most…

Claire Millard

Written by

I’m a leadership coach. I work with driven, high performing executives, startup founders and entrepreneurs

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

Claire Millard

Written by

I’m a leadership coach. I work with driven, high performing executives, startup founders and entrepreneurs

Better Humans

Better Humans is a collection of the world's most trustworthy writing on human potential and self improvement by coaches, academics, and aggressive self-experimenters. Articles are based on deep personal experience, science, and research. No fluff, book reports, or listicles.

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