There was certainly a lot of hype about the keynote speaker taking the stage at this particular event to which I’d been fortunate enough to score a ticket. 

He was a founder and partner of one of the world’s most reputable venture capital firms, a renowned author and an incredibly successful entrepreneur. Certainly deserving of the standing ovation he received before he even opened his mouth. 

Looking out into the audience of hundreds of startup CEOs all proudly wearing their company branded t-shirts or hoodies who had gathered at this awesome venue in San Francisco in 2017, he asked, “What type of leader are you?”. 

Silence. You could have heard a pin drop. 

“Maybe I’ll ask it like this then”, he said. “Who do you admire? Or who is a leader that you aspire to be like?” 

I was expecting to hear the usual responses to this type of question at the time – Steve Jobs, Bill Gates, Barrack Obama. 

“Golda Meir”, someone shouted from a few rows in front of me. The first female Prime Minister of Israel. “Jack Ma” a voice boomed from the back of the event space. The founder of Alibaba. “Adam Neumann”, shouted a guy a few seats to me right”. The cofounder of WeWork. 

“All very interesting choices. But what exactly do you admire about them?”, the speaker asked. 

“She was tough and led with confidence and conviction” (about Golda Meir). “He’s hungry and tenacious” (about Jack Ma). “He’s eccentric but everyone admires him” (about Adam Neumann). 

Back then, our office was in one of WeWork’s very first San Francisco-based spaces and the WeWork team were constantly raving about their leader. To me it felt a bit too cult-like, and his eccentricity and star power would ultimately bring about his downfall, but I digress. 

“And these are certainly all very interesting traits”, the speaker continued. “But today I want to talk about probably the most important leadership trait we look for when investing in founders. After all, sure we invest in companies and in ideas. But ultimately, we are investing in the leaders.” 

Silence once again. 

“Of course, confidence and conviction are important. Tenacity is great, and to be honest the right kind of eccentricity might even impress some investors. But when all is said and done, we look for leaders who can clearly demonstrate a strategic perspective”. 

I learned so much in the 45 minutes that followed. But for me, the most important message I took away was that leaders with a strategic perspective will disrupt their own business before they unwillingly let a competitor disrupt it for them.  

Perhaps you think about a coach or captain of a football team scribbling on a white board in front of the team in the lead up to a big game. Or maybe you think about a chess Grandmaster. In either case, it’s about the importance of thinking and planning several moves ahead as opposed to waiting for something to happen (typically by an opponent) before reacting to it. 

For the purposes of this particular article, let’s combine the terms ‘strategic thinking’ and ‘strategic planning’ into what the speaker at the San Francisco CEO Summit had referred to as ‘strategic perspective’. 

And, as the speaker above shared with his audience of eager entrepreneurs, it’s about being nimble enough to pivot and re-set your direction while being adaptable and ambitious simultaneously. 

This question is particularly important to those leaders (or aspiring leaders) who, for whatever reason, feel that they may be more operational or tactical in their approach to driving their business. 

Whilst there is absolutely nothing wrong with being focused on operations – focused on the people and on the work they are doing, leading with a strategic perspective involves a more proactive approach. As with the football coach or chess Grandmaster I referred to above, it’s about thinking several moves ahead – whether this means weeks, months, or years; and includes thinking about your people, processes, products, new markets, competitors and what (if any) parts of your business might be ripe for disruption. 

Coming out of the pandemic and creating the ‘next normal’ in the workplace (whether this means a remote, distributed, or hybrid environment), it is not uncommon to hear leaders refer to the analogy of “flying the plane while building it”. The pandemic pretty much squashed any leader’s ability to think strategically since it’s highly unlikely that anyone really saw it coming. Every leader reacted (the only logical response at the time) but now that we’re (hopefully) on the other side of it all, flying by the seat of your pants doesn’t equate to leading with strategic perspective. 

Whilst you may still need to focus on your more tactical and operational responsibilities (eg developing and motivating your team, or communicating to customers and other key stakeholders), if you want to add a more strategic perspective into the mix, you might want to consider the following: 

• What will still make your company, product, or service unique in 3 – 5 years? 
  
• What are your competitors doing that might eat up your market share? 
  
• What’s the ‘next big thing’ that might impact your business? 
  
• What might you need to learn about the megatrends facing your industry sector?
   
• What coaching might you seek to help you develop a more strategic vision? 

With the Board, your stakeholders, customers, and of course your own team members. You will welcome and be open to feedback and advice from others (from every level within the organisation) when it comes to your strategy; You will (of course) continue to take risks and innovate; You will encourage thinking and planning strategically as a core foundation to your company culture; and you will continue to help others understand your vision and strategy so that they can, in turn, set and prioritise their own goals. 

Remember hellomonday provides coaching and support to every leader, prioritising development initiatives that result in long-term sustained learning and change, reinforcing habits through curated learning and impactful coaching, and ideally helping leaders understand the importance of demonstrating a strategic perspective.