Building Confidence & Hacking Executive Leadership

What brought you to executive coaching?

I was a coach before I knew what a coach was. I had worked in a number of corporate jobs spanning from very large companies like Amazon and Microsoft to small-to-medium technology-based businesses. Looking back on several jobs after they were done, I realised the thing I remembered most was helping people get to the next level – whatever that was for them.

Those interactions and relationships stood out as my favourite and something I was very proud of. When I found executive coaching, I said: “Oh! This is who I am – this is what I do.”

Your book Hacking Executive Leadership was released earlier this year – what did the inspiration about the book come from?

I kept seeing a lot of the same themes pop up again and again. Everyone had their specific situation or slant, but some recurring themes emerged. I thought, you know, I’m giving this type of guidance to a lot of people and it seems to be helping. How do I get that message to more people? That’s when the idea of a book crept into the back of my mind.

Tell us a little bit about your story and how you managed to go from someone who was once nervous to talk in front of your colleagues to someone who now coaches CEOs on leading team meetings?

Yes! I remember sitting in my first leadership team meeting like it was yesterday. I had just been promoted; I was by far the youngest at the table. I looked around and everyone seemed so professional and so accomplished. We’d go around the table and each leader would give a brief update on their functional area. I was so nervous when it was my turn I that whispered “no update” and looked down hoping people would stop staring at me.

One of the recurring themes from your question before is confidence – and I’ve had personal experience with this one. It’s something I still work on, but after years of aggressive self-improvement, I’ve come a long way.

It’s funny to think about that first meeting now because I work with CEOs on leading team meetings. And, in fact, some of them are quite nervous to lead their first ones!

That’s amazing!  So what are your key tips when it comes to improving one’s confidence?

This is a broad topic and one of my favourites. I’ll give a few quick ideas.

Overall, the best way to become more confident at something is to do it. If you wait to feel confident, you’ll be waiting forever. Act confidently first, the feeling of confidence will come second. Take action. If you don’t do something perfectly, that’s fine. Learn from it and go again. You’ve just made progress. Once you get that first toehold of progress, that’s when you realise: “Ah! I have evidence now. It’s working. Maybe I can do this” and it builds from there. I love working with people on their growth edge (one step outside your comfort zone) – you can get them familiar with it and use it as an indicator that they’re moving in the right direction. They can then say: “I am successful because I ‘fail’ more times than other people will try.”

In terms of communication and presenting, CEOs are “up in front” of people a lot – team meetings, company meetings, conferences, interviews. A lot of people put unnecessary pressure on themselves in these circumstances. Yes, prepare and be at your best. But hold onto a communication mindset vs. performance mindset. You’re there to convey ideas and information that others don’t have. Focus on that. Also, be aware of the spotlight effect. This is where you think everyone sees every little thing you do “wrong”. When, in fact, no one notices.

Then, almost everyone will have moments of: “I’m overwhelmed. I don’t know what I’m doing. I don’t belong here.” If this comes up, go mentor someone. This is a great way to give back and it also lets you see yourself through another set of eyes and remember all the things you do know and have to offer. 

Have you found that female leaders struggle more with their confidence when compared to their male counterparts? How would you explain this?

That’s a great question.

Yes, in general, women have to pay more attention to the optics. There are many times when women are judged on how they look, how they dress, how they sound, how they say things far more than men. I have female clients who are trying to navigate “good old boys clubs”. They are the first woman in a high-ranking role or the only woman in a cohort. Carrying those mantles can have added pressures along with just doing a very demanding job.

I think the reason for this is twofold – men and women are socialised differently and there is a generational element. Overall, women and young girls are taught to be pleasing and to be peacemakers; men are generally taught to not show or talk about emotions and to be more direct. I was talking to a middle school teacher and she described the different ways boys and girls would go about resolving a conflict – she said a girl will be more likely to look at the power dynamics of the group and try to work it to her favour behind the scenes, whereas a boy is more likely to walk up and punch somebody.

If you look at the traditional roles men and women held in society and the workforce in previous generations, it’s pretty one-sided. In fact, I was just re-watching the show Mad Men which is about the inner workings of a New York ad agency in the 1960s. One thing it highlights is how women were treated in the workplace. All the women were secretaries and reported to men. The way the women were treated is shocking. By today’s standards, some of the men are just walking, talking HR violations. I’d actually recommend watching a few episodes of that show – for both men and women – just for some eye-opening context.

I do want to acknowledge the progress that has been made over the last several decades. We have more women CEOs and political leaders than ever before. There’s still a long way to go, but we’re moving in the right direction. Young women today will have role models to look up to and they can see that it’s possible for them to hold these types of roles.

I worked for a gentleman who was in a President role reporting to a new female CEO. He brought his two daughters into the office and introduced them to the new CEO saying: “This is daddy’s new boss, Alison. Can you say hello?”

There are many times when women are judged on how they look, how they dress, how they sound, how they say things far more than men. I have female clients who are trying to navigate “good old boys clubs”. They are the first woman in a high-ranking role or the only woman in a cohort. Carrying those mantles can have added pressures along with just doing a very demanding job.

I spoke with him afterwards and he said it was important to him that his girls see that their dad could report to a woman and that they could run a company one day. I thought that was fantastic and have always remembered it. For your readers who are men, do not discount how much of a difference you can make with interactions like this one.

What would you say to new CEOs building a team?

Well, there are many aspects. Paying attention to who is on your leadership team in the first place is important. Look for people aligned in values but who have wildly different skill sets. Maybe it’s a functional area of the business you don’t have direct experience in; maybe it’s a different perspective that you just don’t have – build in those diverse frames of reference. I’ve seen far too many CEOs take the egotistical route and pick people who just make them feel smart and important all the time.

Drawing on my experience as a Chief of Staff, my main principal is our CEO. We see things through very different lenses – he comes from a finance background and sees things through numbers, market conditions, spreadsheets; I see things through the human element, team dynamics, building people, processes and tools. Neither vantage point is ‘right’ or ‘wrong’, you need both to run a successful business. But we appreciate what the other brings to the table.

What’s one aspect of leadership you think is overlooked?

Self-care. More and more people have this word in their lexicon, which is a positive step. But, in my one-on-one conversations, I still hear a lot of sentiment around: “Yeah, yeah, yeah, I know I’m supposed to do that, Emily – but I don’t have time, too many people are counting on me.” Taking care of yourself and putting yourself in the best position to lead and make sound decisions is part of your job. I don’t want someone who’s had four hours of sleep a night for the last month and is bleary-eyed to be making an important decision about my livelihood or the company I work for.

There’s this great principle in Greg McKeown’s book, Essentialism, which is “protect the asset” and the asset is you. Think of a singer. Her voice is her asset so she would do well to protect it – rest up before a big concert so she can perform at her best. It’s the same with leadership. Do what you need to do to recharge.

What are the most important takeaways from your book in today’s business world?

A key takeaway is adaptability. A leader in today’s world needs to be able to adapt well. This can be adapting to something small like a change in the daily agenda all the way up to navigating a global pandemic. How adaptable are you? How quickly do you realise you need to make adjustments? How well do you deal with uncertainty – can you keep yourself and your team calm and focused?

One thing I saw good leaders do when COVID first hit was up their game in terms of adaptability. In early 2020, CEOs had to adapt in terms of their business model and deliverables and also how they worked with their teams internally. New information was coming out at a pretty rapid clip, rules were changing, and decisions had to be made quickly – do we need to lay people off, which departments, how many, can we stay afloat, can we wait and see or do we need to act now. Leaders who adapted to making decisions more quickly than they would have liked did better than those who resisted.

There’s this great principle in Greg McKeown’s book, Essentialism, which is “protect the asset” and the asset is you. Think of a singer. Her voice is her asset so she would do well to protect it – rest up before a big concert so she can perform at her best. It’s the same with leadership. Do what you need to do to recharge.

So how can one take lessons and ‘hack’ executive leadership? 

Adaptability is a close cousin of uncertainty. A mistake I see leaders make is automatically labelling change as “bad” or a negative.

A helpful motto to remember is change is neutral. Change in and of itself is a neutral event – the subsequent outcome could lead to things you like or don’t like.

Humans by nature don’t like when a situation is uncertain. But that awareness and that moment you realise you’re automatically slapping on the negative label is key. The one beat or pause in between allows you to see the automatic program running. In this case, you’ve fused together “change” and “negative”. Now you can hack that code so to speak and run a new program.

You can choose a belief and mindset that will serve you better. Change is neutral. You’ll make better decisions because you’re not making it from a place of fear or knee-jerk emotional reaction. You have a clearer head and are more objective.

This is just one example. There are many more. It’s a fluid and evolving process as well – the adage: “What got you here, won’t get you there.” There are inflection points in one’s career where the next level up will require something more or different from you. This is one of the reasons why I love being a coach – everyone has their own set of experiences and motivations and it’s about meeting a person where they’re at.

I’d highly recommend finding someone who can be an objective sounding board. This person can point out blind spots or offer observations you can’t or don’t see yourself; they can support and encourage you in the right places and challenge and keep you accountable in others. If you have someone who can do this for you – a friend, a mentor, a coach – it’s a great resource.

Contact details:

Website: www.nextlevel.coach

Book: https://www.amazon.com/dp/B092RPR9RX

Email:  emily@nextlevel.coach