Some thoughts about product, leadership, and teams

I recently had a conversation about what I think about leadership, management, and what my "style" is. It ended up going on a long path about my feelings on growing a team, interacting with others, developing a product, getting work done, managing growth and being pragmatic.

Our great conversation stayed with me afterwards, so I thought I would share a bit about it here.

First recipes, and now IT-LinkedIn-Thought-Leadership? I really am having an identity crisis on this blog, aren't I?

We spoke about what I think about products, the use of AI, how I approach managing teams, hiring for growth, and generally trying to be just a chill and reliable person.

Since I'm partially writing about a conversation, I'll try to organize things in a way that makes more sense on a blog post and do my best to group areas up into sections.

Products and people

To share my opinion on product development, I will use my own one, Barkeeper as an example here (:plug-emoji:).

Barkeeper was initially conceived post-pandemic when I noticed that local bars were having trouble returning their trade to pre-covid levels.

At the same time, most of these smaller places didn't have expertise in one or more of the following areas:

• Building websites
• Online marketing
• Social media management
• Competitor analysis
• Review management
• Basically anything tech related at all

So the vision for Barkeeper was to bring more customers into my favorite places. To do that, I would make a simple to use tool that would build a website, manage online marketing and social media, and provide competitor and sentiment analysis.

My hypothesis is that by improving their online presence and giving venues more easy access to what their customers are saying about them and their competitors, that they will be able to attract more customers and better retain existing ones.

At the time of writing, Barkeeper hasn't fully launched, so I am still waiting to validate the hypothesis. However, the niche and vision are clear.

It's got to have a purpose, reason, and meaning

Our conversation at this point was about how I think about products and generally how companies are dealing with the AI land rush.

I explained how I feel that "AI" has kind of become a marketing term for companies without necessarily reflecting a need or purpose. To me, a tool has a use, and while it exists on its own, it only really is useful when it has a purpose (and is used for it).

To use an analogy: A hammer is always a hammer, but with it you can grab some nails and wood and make a fence. AI is a hammer. AI isn't the fence.

The reason why I bring up Barkeeper is that it uses some AI tools as part of its functionality. The main components being sentiment analysis, text generation, and machine translation.

There's no big buzz-wordy intro for AI in the niche or the vision of the product. The product itself has a goal, and AI tools are part of how it provides its solution.

I feel that for a product or service to be "good", it has to serve a purpose. It has to have a clear passion and vision behind it. It has to matter to the people behind it, and positively impact its target customers.

I'm lucky to have worked at some excellent SaaS product companies both currently and in the past. FreeAgent taught me about customer focus and passion in a very real way. The leadership team were laser-focused on their goal of "democratizing accounting" and delighting their customers. Their example shaped a lot of my views on products.

Properly identifying who your customers are, identifying what they want, and then giving to them are the obvious basics of product development. However, I learned that the real value comes from finding a need and finding or making space to innovate.

More recently through my expanding responsibilities at Tripla, and supported by my background running my own companies, I've learned to be more active and aware on the strategic thinking around product development too.

You have to have a strategy

Strategic thinking is what turns a good idea into an actionable product. It's a little gauche to think about the nuts and bolts of markets, entry, impact, and synergies all at the time when you're working on a side project. However, I think it's critical if you even remotely intend for your project - in this case Barkeeper - to be successful.

For Barkeeper, the Market Fit, and Value Proposition parts of the initial strategy are explained a bit above.

The Business Model is a simple SaaS subscription model with multiple tiers of plans which include different levels of service and functionality.

In terms of Go-to-Market, there are pilot customers lined up to use Barkeeper for their bars and clubs and provide important early-stage feedback to allow for some iteration on the service.

Admittedly, for a new product that is in its pre-launch phase, there are still a lot of areas of the product strategy that I need work on - specifically around customer support and retention.

While we're talking strategy, I really enjoy playing RTS games like Command and Conquer, but lately my husband has got me into Magic the Gathering: Arena (all those cute otters are too much to resist!). It's actually helped me with planning, believe it or not, as you have to plan your moves 3 or more steps ahead to assure victory. Pastimes are beneficial!

In my day-to-day at Tripla (my current employer), my important strategic decisions and thinking are all around the availability of our platform, its security, and the future growth of the service and our team.

Increasing performance or improving reliability has a big impact on how our customers perceive the quality of the service provided. Investigating and embracing new technologies is critical to that, since it helps you and the team keep the proverbial toolbox full, and make sure that the tools it contains are relevant to our ever-changing industry.

This is where strategy has to include how you manage and interact with the people who you work with. This doesn't just mean your direct reports - but everyone up and down the org chart. As a company, you're united to whichever goal the company is working towards and it is important that everyone feels ownership, empowerment, and support, in order to meet the goal.

This leads me on to talking a bit more about teamwork, and how individual contributions can help with the overall strategy of a company.

It's also important to speak up

Among the things that Tripla and FreeAgent have in common is their open culture. That's something I try very hard to actively cultivate in my department and daily interactions with everyone.

If a new feature, a change, or removal of a feature might have a negative impact on how customers feel - then anyone should be able to bring up their concerns and discuss it.

At Tripla we actively practice "disagree and commit". Building consensus is very important (especially in Japan), but can lead to decision paralysis where nothing gets done as the committee isn't satisfied.

Instead, when a new feature is being discussed or specified we are all actively encouraged to review and provide any feedback. Even if we think it is an awful idea. Obviously, with proper respect and reasons for the dissent.

However, once a decision is made, everyone is 100% behind it and has one goal to make it a success.

To me, this is very important. A diversity of viewpoints and opinions can strengthen decision making and make you consider complications that you previously hadn't thought of.

Ok, this is starting to read a bit too much like I am answering interview questions. What is your biggest weakness? Rambling on and on in blog posts.

Keep your team confident and happy

To allow things like "disagree and commit" to work, you have to make sure the environment you foster as a leader is respectful, demure, and mindful. I feel that the best way to do that is to make sure every member of your team knows they can speak their mind on any topic, and feels empowered to do so.

I achieve that on my own team by making sure I am always approachable, never judgemental, and am always as open minded as I can be. Discussion is important for sharing ideas, as mentioned above.

It helps that as an engineer, I am used to receiving and giving peer / code reviews on a regular basis. Being open to having other people explain how something should or could work better has the side effect of making every environment more collaborative. It's clear that critique is about the work and improving the solution to a problem and not about the person.

Another side effect of this is that these kind of collaborative environment self-correct for big egos. People with big egos are not always good team players and it's critical to make sure that your team is balanced and comfortable with each-other.

As an aside, one of my previous employers (many years ago) had a hand-written sign on the wall behind the CEO's desk which said "nobody here is an asshole". It was kind-of the unofficial company motto and it's where I learned how to accept the feedback from code reviews, and provide it to others, with grace and humility.

When hiring, I always consider how well I think a person will react to critique and how supportive they will be in sharing feedback with other team members. In fact, it's a part of my standard interview questions for new hires.

This is a great for new hires and making sure that you have a good team, but how do you get things done after hiring?

It's still critical to make decisions though

While "disagree and commit" is a great way to test out ideas, sometimes discussions need to move much quicker than seeking consensus. This is particularly critical during emergencies like service downtime, critical customer complaints, or security issues.

In these circumstances, I think a leader's job is to support the team and take decisive action. This might involve following predefined emergency procedures or simply empowering your team with a "go for it" and the assurance that you've got their back.

In the hypothetical case of an out of hours service outage, I think, the priorities are:

1. Restore service
2. Identify the root cause
3. Prevent the issue from happening again in the future

With the team, I would discuss the issue and try to help everyone identify the root cause. Often for sudden outages, configuration changes or bad releases are the culprit, so the immediate remedial action is to undo the change.

To me, the important thing is to know when to take action. That requires experience and discernment. Your team trusts your judgement and this is why you have responsibility as a leader.

After service restoration and initial problem-solving, thorough root cause analysis and prevention strategies require broader collaboration. This is where cross-departmental communication becomes crucial.

In this case, I would make sure that the decisions needed to restore service immediately are taken - such as rolling back a bad deploy. Then with the rest of the team, do some smoke tests to make sure service is restored.

Responsibility (and thoroughness) requires that the root cause be identified and the issue be prevented from occurring again. I would not consider the incident resolved until all 3 steps outlined above are corrected.

To achieve this, more collaboration is needed. When a bad release causes the service to go down, investigating the root cause needs cross-departmental communication and when leading the review, it's your job to facilitate that communication.

Using Tripla as an example, such an incident would need collaboration between the Product Engineering team, the Platform Team, Senior Management, the QA Team, and the responsible Product Manager.

These cross-team collaborations can be challenging due to diverse skill sets and specialties. Success here requires empathy and the ability to clearly explain complex concepts across different domains of expertise.

Being a good facilitator and helping align with the vision

With strong empathy, and a clear way to explain even complicated subjects, it's easy to facilitate understanding within a group and help get every stakeholder onboard with a potential solution to the incident.

I feel that these skills in dealing with a crisis are equally applicable in all interactions within a company. My personal philosophy is to be open and friendly to everyone.

As a point of contact, people come to me for help all the time. If I can't help them myself I make sure they are directed to who can. This is a basic thing that I feel sometimes is overlooked. If a coworker comes to you with a problem, they still have a problem even if you can't help them yourself with it - you can help them find help - so do that.

One way to help can be with your ideas and time. Bring up ideas that you think might benefit your customers. They will be discussed and exposed to "disagree and commit" like all ideas, but it's important to share them.

To give a concrete example, I am responsible for security and compliance for parts of Tripla. This lead to me suggesting a project to investigate a third party tool which could support the company's aims in that regard.

Unfortunately, while the tool worked well, and had excellent AI-backed features, it was unusable for any non-English language.

As Tripla has customers all over the world, and we officially support Japanese, Korean, English, Chinese, Thai, and Indonesian - this really wasn't good.

Instead of only rejecting the tool, I came up with a solution. Working with my team, and other in-house expertise, I designed a tool that would work for all our supported languages and meet the basic requirements.

The team and I built this version quickly and planned a roadmap of features and enhancements to serve future needs as the company grows, in line with the vision to expand overseas.

By facilitating this process, we not only solved an immediate problem but also reinforced our commitment to serving customers worldwide.

This experience highlighted how good facilitation can turn challenges into opportunities that align with and strengthen the company's vision.

Effective facilitation isn't just about solving problems; it's about guiding teams to solutions that reinforce and advance the company's overall goals. It requires empathy, clear communication, and a constant focus on the bigger picture.

Wrapping up

This blog post is probably the longest one on my blog - sorry about that and thank you for making it this far!

The main takeaways for what I am trying to say are:

• Empathy and understanding are king, do your best to be a good person and understand who you work with
• Your knowledge and experience are valuable, but must always be tempered with humility
• Always help in any way you can
• Disagree (respectfully) if you need to
• Make sure you have your team's back and you know they will have yours. Lead by strong example of how you expect others to be treated with respect and trust
• Otters are cute

Thank you for coming to my Ted Talk.

My understanding about leadership and my current viewpoints are shaped by a huge number of people over my past 18+ years in the industry. I'd like to specifically thank Kaku, Lake, Kazu, Teppei, Horacio, Olly, Roan, Ed, Graeme, Russell and JB.

You all were and continue to be a source of example and inspiration for me as I learn to be a better leader and improve in my work.