How to Royally Screw up a Product Launch — Twice


We like to think of ourselves as people who stick to our deadlines (I am sure you are the same!). So why do we often miss the deadlines we create in our minds? And why are so many of us overdue in shipping our next project? The new Kayako was no exception – It was overdue almost two years.

The truth that is never told about releasing products is that it will cost you sleep. If you fail to meet the product launch date you announced, it will eat at you. But if you are leading a project to launch, and you don’t make your deadline, the biggest stress is not your own feelings. No, it is the impact on your team’s morale.

Imagine feeling the full weight of failure, not once, but twice. This is what happened to us.

The experience taught me two tough lessons:

  • You can’t build a product on hopes and dreams,
  • When you fail to match the product in your mind with the product you’ve built, it can be tough on you and your team.

You begin to feel that you are the reason the product hasn’t shipped yet. Demons confront you every day. You may start to tell yourself that your team has stopped believing in you, or that they’ve stopped believing in the product.

But you have to move on from these stories. I decided to look to people who had succeeded. Picking up a few books, I dove deep into the pragmatics of launching a product and I discovered something surprising. Who knew launching a SaaS company could relate to a tractor factory?

Line up your 800 tractors

In his book The Great Game of Business, Jack Stack tells a story of working for International Harvester. It was the beginning of October, and they had to build 800 tractors for an international order. But the average output was 5 or 6 tractors per day. With that construction rate, by the end of October it would have put them at 700 tractors short. And what made it worse, was that each day the order was overdue, the international client would charge them a late penalty fee.

Stack could have chosen two routes:

  1. He could have agreed with the rest of the board to keep this information a corporate secret, and started laying people off.
  2. He could embrace the work at hand, be open about the problem, and set out the steps to achieve 800 tractors.

He told everyone the whole story, and rallied the company to complete the order by the end of the month. He put up signs everywhere, “Our goal: 800 tractors.” It was this singular goal.

There were many operational issues to refine. But the key to their success was taking a big problem, and dividing it into smaller obstacles while keeping the goal in front of everyone’s eyes at all times.

If you want things to happen you need people to raise their sights, not lower them. People need big goals, the bigger goals you give people the quicker they blow right past the little obstacles. The broader the picture you give people, the fewer obstacles they see in their sights. Show your employees the big picture, show them the challenge and let them experience the fun in winning the game. – Jack Stack

This is what we wanted: to empower employees to lean into the work and relish the fun of beating the game.

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Kayako’s factory failings

Of all the things I read in Jack Stack’s book, the biggest game changer – that I’d failed to do in the past – was to bring clarity to a product launch. Our leadership team knew what the product looked like but they didn’t know what launch looked like. “Launch” was this ominous unspecified thing. No one knew what it was – we were just expected to get there one day.

Getting to grips with our product roadmap and timelines had become thankless. We kept going back to the drawing board. But it didn’t work, with 14 months of little sleep, we’d failed to build the product, and poorly estimated our development timelines – twice.

The more patching we did the more “unknown unknowns” – to coin the phrase by controversial politician Donald Rumsfeld – were being exposed.

Donald Rumsfeld quote on unknown unknowns is applicable to a product launch and how it can fail

There are known knowns. These are things we know that we know. There are known unknowns. That is to say, there are things that we know we don’t know. But there are also unknown unknowns. There are things we don’t know we don’t know. – Donald Rumsfeld

For every missed milestone – we adjusted our approach to better predict timelines. Eventually, we stopped setting deadlines. We were fed up with letting people down.

We felt that we were the reason the product wasn’t coming to fruition.

We had to rally the company, illustrate the shape of the new Kayako, and we needed to be able to track the process.

Our own shortcomings can be separated into three areas:

  1. We weren’t translating our vision into an action plan
  2. Our progress wasn’t meeting our vision, and we were scared to ship the new Kayako
  3. We didn’t help the team solve our unknown unknowns

The first step was clarifying launch, and the exact steps that would go into it.

Lining up our own tractors: taking a pragmatic approach to building a product

We applied Stack’s methodology to modern day SaaS product development.

The hidden elements in Stack’s story that we needed to take into account were a deadline and shipping on time. Jamie and I are both perfectionists which is good when deployed where it is needed. But for us it meant we kept adding more to the new Kayako. We wanted to be miles better than any competitor. I wanted us to feel proud, and for us to match the product in my mind.

It became clear that we needed to trim down our vision for the new Kayako. Steve Jobs always emphasized getting the product out on time with Apple. His mantra was “just ship on time”—upgrades/updates can always be done later. And LinkedIn’s, Reid Hoffman agrees, “If you are not embarrassed by the first version of your product, you’ve launched too late.”

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Taking Kayako forward with a different kind of leadership

Like Stack, we knew we had to give people information beyond what was needed to do their specific jobs. If you don’t share the big picture of your goals, employees start to feel their work is not relevant.

The essence of leadership is seeing something that does not yet exist and trying to create it. If you don’t have that dream, you are not a true leader. When you start to believe and communicate it as a reality, it becomes a reality.

Rally the team around that single goal

Everybody saw that we’d lost faith, so we needed to rally the whole company. Everyone had to believe in this date.

We knew this would take a huge amount of work, and we needed to show that this time we were serious. The key was to talk about our launch in absolutes—no “if we launch.”

First, I tackled the leadership team. It was vital to get the whole leadership team believing in this date, and communicating the date in absolutes to their departments.

Our next goal was to unite the company, to give the team accountability, and a sense of purpose. Just like Stack’s sign  for 800 tractors, this message had to be in everyone’s faces every day.

  • Jamie and I had t-shirts printed (that we wore every day)
  • We would hold a weekly all hands meeting to mark the success of moving closer to 100% readiness in all areas.



A photo posted by Jamie Edwards (@jmedwards) on

Add clarity to the goal and the exact steps needed to get there

We were held up many times by unknown unknowns. They cropped up constantly, stunting our growth and progress. And they haunted our team’s morale each time we went back to the drawing board.

We were constantly asking, what would it take to build the new Kayako? We added placeholders for the unknowns, and got clarity on each unknown as soon as possible because they had crippled us so badly in the past.

Calculating our own production line: “What would it take to build the new Kayako?”

Just as Jack Stack constantly analyzed and reviewed the production line and the systems in place to help them get to 800 tractors, we had to map the exact steps to take us to a successful launch.

For us, this took the form of a spreadsheet. We  detailed every little step addressing all of areas of development in all departments. Within the launch tracker each department had a list of tasks. Each time a substep was completed that department would be closer to their 100%, and each time a department got closer to their 100%, the closer to 100% readiness we were.

Everything in our launch tracker spreadsheet had to be detailed, and we demanded this process.

There was never anything labelled just “collaborators,” Jamie called this “fairy dust.” We needed an action plan for what is collaborators. Until then it was fairy dust.

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Once Jamie had detailed everything, we had to get the team back on side believing in us and the company again.

Showcasing a cadence of progress

We interpreted this as having an all hands company meeting every Friday at 1pm. We reviewed the weekly progress, and sought to rally the company. We needed the team and they needed inspiration and a sense of excitement only we could give them.

Every Friday we updated our launch tracker. This tool (along with our t-shirts!) inspired the team about the progress they made. It demonstrated they were winning the game. It spurred them on to beat the challenge and be ready on time.

We had to be persistent with the meetings, and insistent on showing progress throughout each week. Each time we demonstrated the strides each department had made towards our goal.

Inspiring a company behind a singular goal

International Harvester employees met their goal of 800 tractors because of transparency and teamwork. Realizing they were winning the “game” helped them meet their goal.

Our launch tracker not only illustrated how close we were to our goal, to give an executive overview of product development. It had to be visually pleasing, and encourage excitement.

Using a .xls spreadsheet is one of the key ways to a successful product launch

And it worked, we launched on time

But what were our keys to success?

We prioritized the spreadsheet

We kept the launch tracker updated. No exceptions! This spreadsheet was a powerful measure  of everyone’s success. Updating that spreadsheet was the last thing we did every day before going home.

Without showcasing our progress, our weekly meeting would not have been so successful. As a helpful boost to the spreadsheet, we also showcased the work of  individuals. At first we called on people for demonstrations, but as we got closer to launch many team members were coming to us asking to showcase their work.

Everyone was focused on the work

The launch tracker brought clarity and focus to our team so we could refine our duties. It compounded the value of everyone working together, and felt like magic to see the progress everyone made. Every day we saw teams overcoming huge obstacles and making giant progress.

Weekly check-ins and updates on progress

We needed to learn that excitement and belief doesn’t come through osmosis. Through the all hands meetings we regained the team’s confidence in us and the product. The goal was never to call out departments that were falling behind. It was for other departments to lean in and help them catch up.

The true genius behind a product launch

The image and dreams we had were strong, and had stuck with us for so long but it didn’t mean our team could read our minds. We had a hard lesson to learn in effective communication.

Taking Kayako forward and focusing on the fundamentals of building a product got us far. But full communication, and cross-company transparency  took us further.

When we prioritized our team, inspired them, and gave them a challenge, the magic happened. The true genius is not what we did. It was the whole Kayako team getting behind it. Without them we would never have achieved launch.

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