Reasons

Nr 1: Flexibility

Work at your own pace, according to your own schedule with no need to co-locate to be able to collaborate.

Nr 2: Deep Thinking

Without the pressure of “thinking on the spot” in meetings, you are able to think deeply and develop creative solutions.

Nr 3: Record-Keeping

Ideas, feedback and solution are documented in one single document

How to make problem solving asynchronous

1. Create a document in a tool that makes commenting easy.

A tool such as:

• Google Docs
• Microsoft 360
• Notion
• Dropbox Paper

2. Write four headlines.

• What is the problem?
• Why is that a problem?
• What are possible solutions?
• Which solution do I recommend at the moment?

Answer the questions above alone or with another person.

Share the document, ask for comments and set a deadline.

Done!

We’ve all been there, dreading this awful retrospective of a project or sprint gone completely off the rails. We probably learnt a lot, but the main gut feeling can be summarized in “Ouch”.

Running a successful retrospective in these situations can be somewhat challenging, especially if you want the team to continue being a team at the end of it.

Here are some important elements on how to run a retrospective that will not end in disaster.

Check your heads and reset your thoughts

Whether you have your retro in the morning, in the afternoon or late in the evening, people need to reset their heads to the retrospective. Maybe they’ve had a crazy commute, had to wait for lunch for 30 minutes and then wolfed it within 5 minutes.

Asking icebreaker question is an easy way fast way of resetting your mind. Some dislike them and think the icebreakers are a waste of time, even then, the moment they start to think about “how silly the icebreaker are”… that’s when it has done its magic. It made them focus their thoughts on something else.

Safe from harm

Make the retro a safe place for improvement by stating that we believe and trust that everyone did the best they could with the information and knowledge they had at the time.

Every now and then I state the The Prime Directive written by Norm Kerth in his book Project Retrospectives: A Handbook for Team Reviews.

Regardless of what we discover, we understand and truly believe that everyone did the best job they could, given what they knew at the time, their skills and abilities, the resources available, and the situation at hand.

Start with the positives alone

This is one most important part of this retrospective. It is super easy to go into all things negative about a disastrous project, but by focusing on good and great achievements as a separate part of the retrospective we will have a record of what we experienced or learnt that felt important to the team.

Run an exercise writing stickies on the topic of everything good about the project.

Before we get going with the nitty gritty of the project we need to remind ourself of everything that was really good with the project, so that we do not forget it.

Let each member walk through their positive learnings from the project.

Group the stickies and ask the group to reflect on them and ask if there is anything that we need to add, again “so we don’t forget about it”.

The improvements and the purely bad

With some positivity towards the project you can now run a usual retro, such as “The Good, The Bad, The Ugly”, “Liked, Learned, Lacked, Longed For” or “Keep, Add, More, Less”. But remember that there is no need to run “The positives” from those retros, since you’ve already asked for them.

Similar to the previous, let each member walk through their notes. Group and reflect. Are there any action points to bring forward to the next sprint or project?

End with the positives

Now you hopefully have a whiteboard full of notes. Positive learnings, bad experiences we don’t want again and things we can improve.

Summarize and end the session by stating: This was a challenging sprint/project, we are pretty awesome that pulled through it. Re-iterate the action points on what we can do to get better, and focus a bit on all the things we’ve that was good and great at the end.

In smaller companies and start-ups it is fairly common that everyone does everything and try to chip in to stay alive. CTO, CPO, Head of Product and Head of Engineering is probably even the same person.

As the company grows, the need for more clarified positions comes apparent. Someone that used to be Product Manager, Team Lead and Engineer now needs to focus fully on where they make most value and this opens up for others to fill their shoes with any of their other roles.

Filling the shoes of a previous multitasker can become quite tricky, since the people who depend on you could hold you responsible for many of the responsibilities the previous person had.

Enter the Roles and Responsibilities workshop to clarify this.

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I’ve run a couple of different session’s of this workshop and it depends a bit on the attendees current roles. With plenty of people and many roles you try to dissociate the person from the role to identify the things they do, that probably needs to get done, but might not part of their role. With plenty of people with the same role you focus on what some people do in their role that others don’t.

Both of them is to clarify what is expected within your role and to clarify what else you do that is not part of it.

“Plenty of people and many roles to clarify”-session

1. Add all names to a board.

Fairly simple, no explanation needed.

2. Take 10 minutes and write up everything that you feel you are responsible for

A lot of stress comes from uncertain responsibilities, things you think you are accountable to do but possibly don’t have a mandate to do.

3. Take 10 minutes to write up responsibilities that you think the others have.

Now it’s time for the other members to give their point of view of what is missing or needs highlighting.

4. Switch the names to the job title that person has

The twist comes when you dissociate the person with their role.

5. That should not be part of your role!

With the roles, instead of names, on top of the column the team goes through all notes and identify the odd responsibilities. Should they be part of that role? Should someone else do it?

Closing the session you identify next steps. How do you follow through on the changes in responsibility?

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“Plenty of people with the same role”-session

1. Add all names to a board

Yup, just do it.

2. Take 10 minutes and write up everything that you feel you are responsible for

A lot of stress comes from uncertain responsibilities. Things that you feel that you are responsible for but possibly not have a mandate to do.

3. Switch the names of the columns

Similar to plenty of people and many roles session there is a twist! Instead of changing the name to role, you change columns between you all.

4. That’s not part of my role!

Look at your new column. Do you think all of these tickets should be your responsibility? Or they part of something else that the previous owner has responsibility over.

Closing the session you identify next steps. How do you follow through on the changes in responsibility?

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“With awareness come responsibility and choice” Amanda Lindhout

By being aware of what others think you are responsible for and setting the right expectations when you are not responsible, will make your life much easier.

And remember, that stuff still needs to get done and even though tasks might not be part of your role it still might be part of your job.

You probably have too many things that you want to achieve

With any project or initiatives more often than not you need to prioritize tasks, cause . With time not on our side, you need a simple way of figuring out what to focus on and what to skip.

Two popular matrices that are widely used are Eisenhower Matrix and Impact/Effort Matrix. With both of them you simplify and condense all data you have on a task and plot them based upon two criteria.

The Eisenhower Matrix

It is easy to focus on urgent tasks and never get to work on the important tasks. Focusing on putting out the fire rather than figuring out what is feeding the fire, is a sure way of continuing in fire fighting mode.

U.S. President Dwight D. Eisenhower realized that we need to spend time on important tasks and not only urgent task, that urgency alone is not the only factor on how important a task is.

Thus the two criteria are Urgency and Importance.

Just Do It!

Tasks with high importance and urgency are easy to prioritize. Just Do It!

Decide When

These are slightly more tricky. Since they are super important, but not that urgent, we tend to forget about them. These tasks need to be scheduled or they might end up in Just Do It!

Delegate

You should try to delegate the urgent but not important tasks or better yet, find a way to automate them.

Try to Skip It

Time wasters, ineffective meetings with no agendas, reports to fill out. Can it be removed, remove it, skip it, kill it!

Impact Effort Matrix

There are some similarities to Eisenhower Matrix, but the focus on Impact/Effort matrix is pretty clear from the naming. Effort is a sense of how much time a task takes or how complex it will be to solve. With Impact we try to measure the importance of the outcome.

Quick Wins!

These low effort and high impact tasks are your low hanging fruits. Pick them quickly!

Fill Ins!

Things to fill out your week. Takes a little time and have some minor impact.

Major Projects

These tasks are probably not tasks. You’ll never get them done without planning and scheduling. Don’t do too many of these at the same time since they need a lot of focus.

Not Worth It!

Stop it immediately. Do nothing in this area.

“Don’t spend major time on minor things” — Jim Rohn

Now take out your physical or digital sticky notes, write down your tasks. Put them on the matrix that suits your need. Then let the discussions begin, cause maybe a task that you think is a Quick Win is a Major Project for someone else.

In the article “The perils of bad strategy” the author Richard Rumelt summarizes some key concepts and stories from his excellent book “Good Strategy/Bad Strategy”.

A good strategy does more than urge us forward toward a goal or vision; it honestly acknowledges the challenges we face and provides an approach to overcoming them.- Richard Rumelt

Richard Rumelt writes that a good strategy has a kernel that contains three important elements: a diagnosis that condense and explain a difficult challenge, a guiding policy on which approach you’ll take and constraints you have while trying to overcome the challenge and lastly a set of coordinated coherent actions which together will solve the challenge.

This sounds awfully similar to the Objective and Key Results (OKRs) popularized by the likes of Google at the end of the last century.

The briefest history of OKRs.

OKRs is a very popular framework for setting goals on different levels of a company. It sprung out of Peter Drucker’s “Manage by Objectives” coined in the 1950s and later improved by Andrew Growe over at Intel in the 1960s.

An inspiring Objective

Objectives are a description of how we see the future. A quote that is inspiring, sets a direction that is qualitative and hard to achieve.

• Where do we need to go?
• Why do we need to go there?
• What kind of constraints do we have?
  Similar to Richard Rumelt diagnosis and guiding policy, the Objective deals with declaring and clarifying the challenge.

The constrains of Key Results

Key Results are how we measure results and progress towards achieving an Objective.

Key Results are like latitudes and logitudes in the background of Google Maps. Informing us when we’ve made wrong turns, if we’re progressing as expected and when we’ve arrived at our destination.

If you write your important KRs before you dig deep into initiatives or actions will also help you from jumping to conclusions on how to solve the problem. What if there are multiple ways of getting to the goal? What if you actually arrived at your destination faster by taking another path?

While some part of the Objective states the guiding policy for your strategy, the Key Results are equally important as constraints.

Initiatives and coherent actions

Initiatives are the OKRs way of clarifying coherent actions i.e. What kind of work do we need to do to get us there?

OKRs and Good Strategy

Good strategy gives us clarity and acknowledges the biggest challenges we have a company. OKRs is one great way to clarify and work with that strategy.

OKRs is a bridge between a Good Strategy and Execution.

If you are anything like me and facilitating plenty of meetings or only have a few meet coming up. There is an easy template or acronym that you can use for planning out your session.

Each of the letters propel you into the next one. Intent gets you half way to what you actually want as an outcome. With that expected outcome you can start planning an agenda, where you start with the end goal in sight.

Intention

What do we intend with the meeting? Why even have it?

Desired Outcome

What specific results do we want to have achieved at the end of this meeting?

Agenda

What will we do at the meeting and in what order to achieve the expected results.

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Sometimes this is enough for a great meeting. It takes a couple of minutes to write, but it highly improves the meeting. When I facilitate longer sessions I add the last three letters of the acronym.

Roles

What roles and responsibilities are there for the meeting to run smoothly? Who facilitates, participates, documents? What is expected of the participants.

Rules

What kind of rules do we have in this meeting?

Should we practice active listening and not just wait for the moment to state your point?

Should we use some way of indicating who talks and how to hand over the mic to someone else, especially valid when doing a hybrid meeting with people both remote and on-site.

Should computers or mobiles be used when we run a meeting where everyone is in the same room?

Law of two-feet i.e. Leave if you don’t contribute?

How do we take minutes and where are they stored?

Let the participants come up with other rules that they want to include.

Time

How long is the meeting, will there be breaks?

Read slightly more over at https://toolbox.hyperisland.com/idoarrt-meeting-design

John Barrows, sales professional and writer of the book “I want to be in sales when I grow up”, talks about three different types of people that advocates your products within the companies they work at: Fans, Coaches, Champions.

Fans

These are the end-users of your products. They love your products, they will talk someone’s ears off evangelizing your product. They have no real impact of decisions or budget.

Coaches

Coaches help you navigate the map of a company. Who to talk to, when to talk to them, and what is going on at the company. “You didn’t hear it from me, but… this is what’s happening”.

Champions

These are the people that can take a chunk of the budget. They might not have direct authority, but they have a seat at the table when the conversations are happening. At that same table others will be advocating their favorite so make sure your champion has the correct data and arguments to advocate your product.

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Do you know if your advocate is really a champion, fan or coach?

As I mentioned in the previous post about growing pains, one regular pattern seen when growing past 50 people is the shift from direct communication to processes.

While it is easy to believe that processes could solve communication and vision challenges, this is seldom the case.

Hey there! You are not following the process!

Sure, we could always point at the process and say “Hey there! You are not following the process!“ And hope that your colleagues changes behavior, but that usually has no long lasting effects, especially when there is a believe that “what got us here, will take us there”.

There is a reason a company succeeds and grows, and it is probably credited with founders’ core values. Customer-centric, adaptability, collaboration, deep technical skills, “we can do it”-mentality to name just a few.

When these rather informal values go through the transformation to become documented processes a lot of agility and flexibility are lost on the way.

Photo by Mark Duffel on Unsplash

Rules and processes have a tendency to be absolute and we need a different way to move forward with our vision and at the same time have the opportunity to steer away from it temporarily when needed.

Similar to how the agile manifesto has values that captures both sides of an argument and favors one, so could a company capture its guidelines.

That is, while there is value in the items on the right, we value the items on the left more. - Agile Manifesto

Instead of writing a process around “Choice A versus Choice B” write guidelines with focus of picking one over the other, “Choice A over Choice B”. Making it easier transparent when we sidestep, but that is ok. Also making it easier to move forward on the vision.

Some examples of guidelines:

• Money over Glory
• Support existing customers over acquiring new customers
• Subscription over One-Time Payment
• Improve existing products over Building new products
• MVP over Big Bang
• Collaboration over Silos
• Team players over Rock stars
• Done over Perfect

Similar to the agile manifesto, while there is value in the items on the right, we value the items on the left more.

While there is value in formal processes, I value the agility in guidelines more.

Read this great article about Molly Graham’s experiences with companies facing challenges during rapid growth and hiring. Managers should focus on normalizing and confirming feelings, their employees feel when change happens in at a rapid pace.

As a leader, you want to head it off at the pass and proactively say, ‘Hey, this is what you can expect to feel during this time of growth. It’s pretty universal‘. - Molly Graham

Rapid growth could mean that your employees are challenged by changes in roles or responsibilities. Certain parts of their work or responsibility, where they have done an excellent job, no longer belong to them. By focusing on the vision and the future and help the picturing it, it eases the transition.

One of the best techniques for getting people through job-change anxiety is to help them picture the reality of their next job and the size of the opportunity. - Molly Graham

Graham also sees patterns when companies grow beyond a certain amount of employees.

We used to be a family, now we’re a company!?

Around 30 to 50 employees you go from being a family where everyone knows each other and can strike up a conversation at any time. Communication is easy and direct. At 50 employees you’ve reached the level where you are a real company, not just a small team.

Everything that used to come naturally is now a struggle. - Molly Graham

While it is easy to focus on defining complex processes to overcome the need for a clearer way of working, you should focus on the principles and guidelines you wish to follow.

We can still change the vision and mission with ease

From 50 to 250 it is still easy to get your message across the company and to change the trajectory of the company. Beyond 250 employees it mostly depends on what you did well before.

A lot of how this phase feels has to do with how good of a ‘parent’ you were earlier on. - Molly Graham

In summary

How we hire and look after the first 100 employees will have an impact and set the tone for the next 200. Be good early on, establish guidelines rather than processes. Be transparent and open about growing pains.

Many moons have passed since I was introduced to the term psychologically safety and I realized that a freshen up was needed, clarity on what we mean when talking about building a psychologically safe workplace.

Psychological safety is a belief that one will not be punished or humiliated for speaking up with ideas, questions, concerns or mistakes. - Amy Edmondson

I found this great TedX talk by Professor Amy Edmondson that coined the term back in 1999.

My main takeaways on building psychological safety are:

1. Frame the work as a learning problem, not an execution problem. We have never been in this situation before, or for long, and we need everyone’s brains and voices in the game.
2. Acknowledge your own fallibility. Say simple things like “I might miss something, I need to hear from you…“.
3. Model curiosity. Ask a lot of questions.