Digital transformation leadership strategies do not match up with traditional IT leadership principles. Make sure you're using approaches that set teams up for success
5 weird questions to ask about your leadership style
We are bombarded with stereotypes of the "right" sort of leader: Use these questions to shake off those notions and learn more about your own strengths and weaknesses
“It’s hard to lead a cavalry charge if you think you look funny on a horse,” wrote Adlai Stevenson. Indeed, understanding and embracing your own leadership style is crucial to truly stepping up to the challenges of leadership in the digital age. With technology very much in the spotlight, IT executives are on stage as never before – and challenged to think much more deeply about not just what they lead, but how.
That being said, figuring out who you are as a leader can be as difficult as drawing your own face from memory. Your behavioral traits are so intensely familiar and closely-held that articulating them (to yourself or others) can pose a significant challenge. Moreover, we are constantly bombarded with stereotypes of what the "right" sort of leader looks like (anyone from Steve Jobs to Dwight Eisenhower), and shaking off these cultural apparitions is a task in and of itself.
[ Do you wish you were a more nimble leader? Read also: How to boost your agility in 24 hours. ]
Five very strange-sounding questions, though, can help you get started on the journey of understanding your leadership style.
The answers to these questions do not paint the entire picture: Think of them rather as the lit match that illuminates the opening of a vast passageway toward deeper comprehension of what kind of leader you are. These questions should breed more questions, which should breed further questions, and so on.
The five weird questions are as follows:
Are you a dog or are you a wolf?
"Wolf!" you instinctively protest. What business leader wouldn’t want to be associated with a brave hunter, rather than a house pet?
Look at the question through the lens of a recent study, though, in which dogs were able to successfully retrieve a treat that wolves could not. The dogs’ secret? When they could not get the treat out of the cage in which it was housed, they gave up rather quickly and made eye contact with humans nearby to ask for assistance. Wolves worked on the problem longer, and did not ask humans for help.
In management terms, the dogs were collaborators/delegators, whereas the wolves were … well ... lone wolves! Both leadership styles are needed – those who collaborate or delegate readily can work well with those who are willing to unilaterally attack seemingly unsolvable problems – but interestingly, some scientists have argued that in nature, dogs have found the more adaptive strategy. After all, there are an estimated 525 million dogs in the world, and (sadly!) only 200,000 grey wolves – picking the right collaborators, in the view of those scientists, seems to have been a winning plan. Food for thought in the era of the "Open Organization."
Are you an impressionist or an abstract painting?
This question does not pertain to actual physical appearance (e.g. a Monet forehead or a Picasso nose). Rather, it pertains to how easily your personality is understood by others: do people "get" you easily?
Like an impressionist painting, do you provide a series of small impressions that add up to an easily comprehensible whole? Or like an abstract painting, do you provide a less structured, less easily understood, but equally meaningful experience to those who interact with you?
Both leadership types can embark on impactful development journeys. The "impressionist paintings" can work to ensure that the more structured image they’re presenting is in fact what they are seeking to project, and can seek to change the shading of impressions they’re delivering.
The "abstract paintings" can seek feedback from others to understand better how they are being interpreted, and like their "impressionist" colleagues, can seek to shape how they are representing themselves. Both may want to steal from each other’s playbooks, with those who are easily read becoming more captivating by being incrementally more enigmatic, and those who are enigmatic becoming more accessible by projecting a more comprehensible vision of themselves.
Are you an index finger or a thumb (or a pinky finger)?
Many cultures use the index finger to point and indicate direction. As a "great precision performer," it has the greatest range of motion of the fingers, and seems to lead the motion of the hand. As a leader, if you’re an “index finger,” you may be charging forward, often in a position of P&L leadership, taking on specialized challenges with ease.
In contrast, if you’re a "thumb," you excel in driving a support function. Everything you do revolves around matching up your skill set with that of others to allow the organization to (forgive the pun) grip ahold of challenges. Thumbs are stumpy-er and less glamorous … but crucially, their utility distinguishes humans from all other animals. Similarly, excellence in support of a business may provide sharp differentiation from competitors.
And intriguingly, research tells us that the lowly pinky finger (teamed with the thumb) may actually be a more critical player on the hand. "Pinky fingers" may be a third, unexplored leadership type – unrecognized but a critical team player who is actually more essential than other high-profile colleagues.
So if you’re a thumb or a pinky finger, your effort should focus on driving excellence in complementarity to others; if you’re an index finger, you’ll want to hone in on exploration of new realms, while always contextualizing your own efforts to the work being done around you.
Are you a mountain or a lake?
We’ve all worked with a "mountain." They are highly visible regardless of the leadership "landscape" around them; their outgoing natures (like the thick vegetation at the bottom of a mountain’s slope) immediately and take in and envelop others. Engaging further can prove more difficult though, similar to the increasingly inhospitable terrain as one climbs a mountain.
"Mountains" can develop their leadership style by choosing to engage more deeply with a handful of key stakeholders – letting them enjoy the view at the summit, as it were.
"Lakes," on the other hand, can often be invisible until you stumble upon them, but then often offer tremendous richness the deeper you go. For "lakes," the central leadership challenge is improving their visibility, which can feel uncomfortable or even flat out wrong (but will yield tremendous benefits for themselves and their organizations).
Are you a merry-go-round or a roller coaster?
This question relates to how others experience your projected emotions. Merry-go-rounds feel safe and predictable: Their motion is constant, and one is never too far off the ground. Roller coasters, with their vertiginous climbs and dramatic dips, can be exhilarating but also off-putting to those do not enjoy the sudden shifts in G-force.
The IT world often has a natural distrust of "roller coasters" – which can lead to some interesting interactions when digital efforts bring IT "merry-go-rounds" and marketing department "roller-coasters" into the same room.
Knowing in which group you fall – and modulating your emotional energy up or down as needed – can be an important part of leadership development. After all, while it may be amusing to interact with a "merry-go-round" who believes they offer the emotional excitement of a "roller coaster," it can be downright unnerving to do business with a "roller coaster" who falsely believes they project the calm emotional tone of a "merry-go-round!"
What if you don't fit into these categories?
Now, you may read these five questions and think, "I don’t fit neatly into these categories! I’m a dog and a wolf! I’m abstract and impressionist! I’m a mountain and a lake!" You may feel like an index finger some days, a thumb on others, and a pinky on the really tough days. Emotions can be consistently inconsistent – periods of being a merry-go-round can alternate with those of being a roller coaster.
In leadership as elsewhere in life, clear and well-delineated dichotomies are often mirages. But thinking about the above five questions – and about the extremes represented in each binary – can help spur you to further explore your leadership style. That search for understanding differentiates leaders who simply tackle day-to-day challenges from those who have the courage to ultimately be extraordinary.
[ Want more wisdom from Melissa Swift? Read also: Building digital culture: Think like a marathoner, not a sprinter. ]