The lessons the books don’t write about

The journey to be an authentic leader with Jane Austin

This month's Confident Product Leader interview was terrific. Talking with Jane Austin we explored her journey into product leadership and her evolution into the experienced C-suite leader she is today. The discussion shares vulnerability, imposter syndrome, the dangers of rigid leadership, culture frameworks and the importance of leadership well-being.

Once a month, I invite a guest to share their experience developing as a leader. I call it Honest Habits. I ask them to be vulnerable in sharing their stories and learnings, and I am grateful to Jane Austin for participating. Jane has impressive career highlights, including ex-Director of Product and Design at Moo, ex-Director of Product and Design at Babylo, and time at Telegraph and GDS. 

Jane had an abrupt welcome into the world of work. After graduating, she landed her first job during the dotcom crash, which was not an ideal time. After the first employer went bankrupt, she found her entrepreneurial flare. She used her contacts and built a design agency. This was her first experience as a leader, and running this business taught her many lessons as she won awards, struggled with P&L and eventually sold the company. 

I didn’t value my time

We started the conversation by digging into that early leadership experience running a design agency. This entrepreneurial spirit was not paying off. One key challenge was being comfortable with charging for her work.  On reflection, Jane recalls a level of imposter syndrome resulting in undercharging for work. This is not unique to Jane’s journey and is a common topic in my leadership coaching work.

Her words felt very familiar to me from multiple conversations with product leaders. Jane opened up, saying, 

“I felt guilty charging people. I felt like, Oh my God, why would they pay me? This was imposter syndrome. I would not charge for my time if somebody wanted amendments to a design. I felt it was my fault for not getting it right the first time!”

“I learned a lot from this. I realised I didn’t value myself enough, and I didn’t value my time. It was an early struggle which I had to work through to grow.”

It is an excellent example of a critical step in most leadership journeys repeatedly encountered - the importance of valuing yourself! If you don’t value yourself, it prevents you from making good decisions and supporting your teams effectively. A previous Honest Habits interview with Stephanie Leue shared similar challenges. 

You have to understand the nuts and bolts

But it is not just self-confidence and self-belief; leaders need to understand the business model and different dimensions. This is one of many differences between being an individual contributor and a leader. 

Jane recalled her frustration as an individual contributor when the business was comfortable ignoring a poor user experience and leaving it sub-optimal.

“I remember seeing some users struggling with something during research and getting angry because the business wasn't going to fix it. The question was, why weren't they fixing it?”

Jane explained that as a leader, you must consider the “nuts and bolts of the business” and recognise the importance of prioritising business outcomes. Understanding the commercials and recognising her value felt like defining milestones in Jane's early days in leadership. 

Not everyone will like you 

As we move on from the first agency and jump to her next leadership position, she remembers the stress one individual in her team created. The person just seemed difficult. In hindsight, there was a personality conflict. This person would always be late, complain, and never appear to enjoy the work or help others on the team. 

Jane admits, “It was an absolute nightmare… I used to worry about them liking me.”

I am sure many up-and-coming leaders face this dilemma as they read this article. It feels like a right of passage as you develop into a leader. You have to recognise that not everyone will like you, and not everyone will agree with you, which is ok. Early in my career as a leader, I remembered a similar situation. I was torn with emotional pressure, wanting a particular individual to be positive with me instead of constantly complaining. As young leaders, both Jane and I struggled with the battle of wanting people to like us. 

Jane revealed, “I had this epiphany. Hang on a minute, I don’t like them. Why does it matter if they like me? It doesn’t. I don’t need to be liked. I just need to be respected. This was the moment I felt I had become a leader rather than somebody in the team.” 

This epiphany was more significant than it might first appear. It gave Jane the confidence to stand up to the individual and unlocked an authentic leadership style that had been evolving. After this moment, she embraced being clear and direct. 

Don’t bottle things up

Jane’s leadership style evolved after these critical milestones and stuck with her throughout her career. Her style is clear and direct with positivity. As we chatted about being transparent and keeping working relationships free of clutter, I was reminded of Kim Scott's book Radical Candor. Kim discusses “bringing your whole self to work” when building relationships. As Jane discovered before this book was written, a culture of open communication will improve performance and must be embraced by leadership.

Jane joked, “I think also being Glaswegian really helps”, but went on to explain what good looks like to her, “being really direct and saying what you mean, in a positive way, not storing things up, telling people that's not okay, but this is why. Leaving them feeling better for it rather than awful.”

Being clear on non-negotiables and why behaviour needs to be different is vital in being a successful outcome leader if done with care and sensitivity. This is a vital lesson for us all. 

Asking questions beats telling people what to do

Jane’s interest in commercial workings and value creation saw her migrate from design and UX towards product management. Her leadership role model was Chad Jennings, CPO at Moo.com, when Jane worked there. She learned from Chad the power of asking questions instead of telling people the answers. To do this authentically, the best leaders believe that others can find a better answer. 

The habit of questioning is a key ingredient to a servant leadership style, which I frame as Outcome Leadership. In a previous edition of the Confident Product Leader, I wrote about how a leader's questioning can unlock innovation. 

Jane explained how Chad didn’t just ask questions which helped to stay focused on what mattered but also made it safe to fail. If leaders are challenged with questions while making mistakes and are viewed negatively, then the questioning becomes an interrogation. Jane works hard as a leader to create a physiologically safe environment and encourages experimentation. She remembers feeling judged by senior leadership in the past instead of learning being celebrated. As a C-suite senior leader, she ensures she doesn’t repeat the same mistakes. 

The whole point of hypothesis-led design is to experiment; the most significant learnings often come from when stuff fails. Unfortunately, it is only too familiar for teams not to feel safe to fail. Outcome Leaders like Jane buck this trend, and the results speak for themselves!

Reflect on emotion before reacting 

We talked about learning from mistakes, and she shared a story where she let her emotions drive her reaction as a leader. Sometimes emotions get the better of us, we get annoyed, frustrated, or even angry and react to those emotions, resulting in a poor decision or ineffective communication. 

I remember being in a leadership role at a young age and, in hindsight, reacting and letting passion drive hasty behaviours. Today, I coach many leaders on self-awareness and empathy to help them overcome this natural behaviour. Jane’s story shared how today, as an experienced leader, she operates a calm style. Working with a coach, she evolved from being emotionally empathetic to cognitively empathetic. This is pivotal in handling a crisis, politics or toxic individuals. Jane shared a crucial takeaway: learning to be less attached emotionally while remaining authentic. People generally behave the way they do for reasons they feel are good; this was a light bulb moment.

I covered different types of empathy in a previous edition of the Confident Product Leader.

Look after your wellbeing 

Senior leadership roles are demanding. They frequently involve high pressure, difficult decisions, multiple perspectives that need considering, political relationships and long hours. So many leaders forget to look after themselves. Jane shared, “We can’t look after the team when we are struggling with stress levels”. 

This lesson from Jane is one every leader should listen to. Looking after your well-being is a priority and can take many different forms. To look after myself, I meditate daily using the Head Space application, participate in a weekly yoga class and frequently mountain bike in the great outdoors. 

Jane pointed out, that in a senior leadership team, it often takes time to recognise the team you are in is the leadership team with your peers. It is easy to focus only on the teams you manage. To perform at a high level, the business needs this team to understand one another and consider each other's well-being. The company will suffer when the leadership team is at odds with each other. 

The Competing Values Framework

We chatted more about the onboarding process of new leaders. Jane shared, “I struggle with the idea that when you enter a new business, one of the first expectations is to transform product vision because you don't have the context. You will likely have it wrong and need to understand the business deeply. So, I have a very structured three-month plan of activities before making changes. One of the things I do when I join a company is use the Competing Values Framework. I love this mapping exercise.”

I had yet to encounter this framework from Cameron and Quinn, which sounded very useful. Jane explained it to me. 

“It has two dimensions. One dimension is allowing flexibility and discretion versus stability and control. The second dimension is focusing internally and making sure everyone's aligned versus focusing on the market and being differentiated in the market.”

During her first few weeks in a new organisation, Jane will chat about the values and sometimes run a questionnaire to understand the situation best. If you know what the culture is, then you know what the challenge is to achieve transformational goals you may have.

Jane enlightened me, “If people aren't aware of what the culture is and that the culture is antithetical to what you're trying to achieve, you're going to struggle. So, I like to frame the culture and help people understand where we are. You can use tools to try and move from one to the other.”

This is a tool I am going to learn more about; it may feature in a future edition of the Confident Product Leader.

Friction Pyramid

Jane has repeatedly joined companies in leadership roles when they were at an inflexion point, driving transformational change. She has developed her framework to navigate improvements. It's a pyramid showing the future as your strategy. 

She explains, “The friction is between the things you’ve already built and how it is working and how you can improve it”. 

Understanding the friction unlocks different strategies and helps recognise your position in the market. Product strategy must consider user friction, including the user's emotions. Understanding the metrics behind the frictions puts a new view on the roadmap and the product strategy. 

Jane promises, “At some point, I will write a blog to share this in detail.” - maybe a guest edition of the Confident Product Leader?

Don’t keep everything in your head

Leaders must switch contexts and manage many ideas and thoughts to operate effectively. Jane shared a secret that she uses the ideas from Tiago Fortes book, The Second Brain. The structured and trusted approach to managing tasks and ideas saves significant cognitive load. 

I advocate for David Allen’s Getting Things Done, which sounds similar. 

Jane uses the Second Brain approach for everything, “Every morning, I can check in and go, okay, what have I, what do I need to do? What have I forgotten? Then make sure that I'm being structured and putting my effort in the right place.”

Jane shared how being structured with time and task management means “I can keep my promises to people”. 

What works at FAANG doesn’t work everywhere

I ask all guests on the Honest Habits series who inspire them. Jane was inspired by leaders she worked with, specifically Chad Jennings and Meri Willams. She also remembers, “Watching the early team at GDS was amazing, very focused and stuck to a story to get everyone bought in.” 

While she has never worked with Teresa Torres, Jane enjoys her content and finds her work inspiring. 

As we chatted about inspiring people, we strayed to leadership approaches that have been wholly uninspiring. We swapped stories about the stereotype “Tech bro” arriving from FAANG at scale-ups with a rigid playbook and justification: “That's how we did things at [Insert one of FAANG]”. 

An anti-pattern for inspiring leadership is to assume that an approach that worked in one company will succeed in another. Large IPO-ed tech firms with tens of thousands of staff have very different politics to navigate from the leadership perspective; the approach to dealing with politics of this size is inappropriate in smaller-scale companies. 

This is a great takeaway to end the interview: outstanding leadership demands fluidity. If you are rigid with your approach, you will not be the best you can be. This counts for staying in one firm as it grows and transforms or hopping between organisations. 

I am very grateful to Jane, such an excellent guest.