Digital Transformation | 12 MIN READ

17 Common Mistakes the Best Tech Leaders Avoid

Becoming a great leader in the tech space takes more than a great new app idea or a large stash of investor money. Successful entrepreneurs are able to rise above their peers in part because of their ability to learn from past mistakes, either their own or ones committed by their peers.

Doing so is difficult, no matter how high up on a company’s totem pole you are. As a result, mediocre managers, executives, and CEOs feel far more commonplace. Some leaders even think they’re exceptional when all the evidence points to the contrary, including the shocking revelation that 80% of employees believe they could do their job without a manager.

This lack of trust and disengagement continues to have a devastating effect on the global workforce. A 2019 Canadian survey states that 2 out of 5 employees leave their jobs because of a bad boss, while other reports paint a grim picture of a labor force that feels undervalued.

So what’s the secret sauce that separates the most successful tech leaders from their contemporaries? Why do only a select few men and women flourish in the IT and/or startup worlds while the vast majority of others fail?

In short, they recognize what to do by first learning what not to do.

In this blog post, I’m bringing you a list of 17 common mistakes that superb leaders avoid making. From the emotional to the tactical, the ideas laid out in this article have been echoed by many of the business world’s top dogs.

Let’s get started!


1. They Let Their Beliefs Do the Talking, Not Their Job Title

If you want to become a leader that your stakeholders, investors, and customers believe in, you need to earn their trust with more than just your job title.

This notion exposes the inherent flaw in hierarchies, where being a manager or executive implies that you’re operating at a higher level than those under you, which is never the case. For example, Steve Jobs may have dreamt up the iPhone, but he wasn’t building them with his bare hands. Does his CEO title automatically make him better than those who did?

Successful executives use what they stand for to impress people instead of their lofty job titles. Remember: humans respect other genuine humans, as opposed to blindly trusting the label next to a name.


2. They Focus on Collaboration Instead of Micromanagement

Almost everyone has been subjected to micromanagement. It’s no secret that it’s an undesirable trait in a boss. So why do overbearing leaders still prevent so many organizations from reaching their full potential?

The answer lies in a leader’s ability to foster a collaborative environment that values idea-sharing, delegation, and autonomy over control. You may disagree with a staffer’s idea or their methods, but if you always insist on doing things “your way,” why hire a team at all? Why not just do everything yourself? Oh wait, that’s both unscalable and unsustainable.

As Steve Jobs famously said, “it doesn't make sense to hire smart people and tell them what to do; we hire smart people so they can tell us what to do.” It’s a pivot that, in large part, separates the contenders from the pretenders.


3. They Aren’t Afraid To Make Unpopular, Gutsy Decisions

I’ve blogged about risk aversion before, but it bears bringing up again here as a massive roadblock for entrepreneurs looking to take that next step.

If you’re unable to make gusty, potentially unpopular decisions, then your industry’s status quo will automatically become your company’s ceiling. Embracing change and regularly push your business outside its comfort zone is a necessary part of growing and scaling operations.

Facebook’s Mark Zuckerberg put it succinctly: “The biggest risk is not taking any risk. In a world that’s changing really quickly, the only strategy that is guaranteed to fail is not taking risks.”


4. They Can Point the Finger At Themselves Instead of Everyone Else

With gusty decision-making and an emphasis on innovation comes the prospect of coming up short. Mistakes and miscalculations happen. What’s important is a leader’s ability to hold themselves accountable.

It’s easy to point the finger at someone else. In the heat of the moment, it’s even easier to make things too personal out of frustration, focusing on assigning character flaws instead of learning from those missteps. The best leaders don’t take the easy way out.

When lesser entrepreneurs throw their employees under the bus, sometimes in embarrassingly public fashion, it’s typically because they’re more interested in making excuses than being proactive about any next step(s). In the words of Lou Holtz, “the man who complains about the way the ball bounces is likely to be the one who dropped it.”


5. They Invest in Employees Instead of Stymying Them

A big sticking point in the current labor market is leaders who don’t invest enough in both the individual and collective growth of their staff members. In fact, only one in four employees feel that their companies have gone above and beyond to help them do so.

In some circles, the traditional notion has been that employers aren’t responsible for that kind of growth. The student is responsible for learning, not the teacher, as it were. That viewpoint is rapidly fading, however, with career experts like Marc Cenedella encouraging professionals to quit if they haven’t picked up a new skill or idea in six months on the job.

One can also question the validity of a hiring process that doesn’t come with long-term investment. If you’re not going to do your utmost to continually upgrade an employee’s skill set and knowledge base, how long can you reasonably expect them not to look more fulfilling pastures?


6. They Treat Every Stakeholder With Respect

As the leader of an organization, you don’t always have to agree with every stakeholder you interact with. Disagreements and constructive conversations about solutions are normal. However, those conversations are only constructive if respect if bake into the interaction.

Sure, this isn’t a novel idea. But too many managers, especially in tech, treat employees like replaceable parts instead of people. Once you lose the respect of your employees, the resulting negative atmosphere is contagious and will seep into your customer experience. I guarantee it.

In the same way that praise is earned and not taken for granted (more on that in a bit), so is respect. Without it, how are stakeholders supposed to buy in? As Confucius said, “without feelings of respect, what is there to distinguish men from beasts?”


7. They Make an Effort to Talk Less and Listen More

Let’s talk managers or executives participating in meetings. The most productive version of that scenario is one where the leaders present do more listening than talking.

Being a great leader involves being a great communicator. Succeeding at the latter first requires engaging with ideas instead of talking over them. In essence, entrepreneurs who have their team’s collective ear are the ones that really hear what others are saying, instead of spending every waking moment wishing they were heard.

There is also a direct correlation between the inability to listen more and the phenomenon of employees feeling undervalued–probably because they’re not being heard often enough. Lifeworks reports that 76% of professionals who don’t feel valued actively seek out an exit strategy.


8. Their Decision-Making is Fueled by Humility, Not Their Ego

Plenty of decisions made by leadership are fueled by egos, closed-door agendas, and so on. Conversely, the best tech entrepreneurs infuse their stances with a sense of humility, focusing on how they can enrich the world they live and not on lining their own pockets.

Decision-making rooted in humility also means checking insecurities at the door and not allowing any need for external validation to get in the way of smart, logical choices. Defending one’s ego is never a reason to make seismic changes that affect stakeholders and investors.

The difference between humility and ego is personified in the Jeff Bezos tweet below. When you’re continuously reminding yourself how much room you still have to grow, you’re already doing much better than so many other leaders out there.

9. They Don’t Need Anyone to Stroke Their Ego Either

Even if external validation is taken out of the equation, another common leadership mistake is to seek out internal ego-boosting opportunities to fend off any insecurities simmering beneath the surface.

When leaders steal minutes away from their employees for validation, they’re putting undue pressure on them to agree. All the while, productivity goes down. It’s no coincidence that board rooms full of “yes men” (and women) rarely generate new, innovative ideas.

At the end of the day, managers and executives must distribute more praise than they expect to get in return. As Cullen Hightower noted, “Our ego is our silent partner-too often with a controlling interest.” Avoiding that scenario is a key step towards leadership growth.


10. They’ve Cut Themselves Off From Watercooler Gossip

If a manager or executive becomes entrenched in a gossipy office clique, it can spell certain doom for their professional relationships, never mind the toxic company culture that can spring to life as a result.

Again, not a new concept, but gossip reflects negatively on everyone involved, not just the bosses. There would be no supply if there weren't a demand. That said, if leaders can’t establish and maintain boundaries, as well as sidestepping collusion, there’s no chance their charges will ever do the same.

Gossip-hungry leaders are insecure leaders. Those who can cut themselves off from the watercooler talk are the ones who, by default, will get more done. Everyone involved has better things to do, don’t’ they?


11. They Let Numbers, Not Half-Truths or Lies, Back Them Up

Being a tech leader in an age where consumers can be boiled down to a collection of data points means numbers, not baseless opinions or lies, must win out.

Now, your organization’s mileage will vary depending on its size and level of IT investment. But, as Forbes’ Bernard Marr points out, “data should be at the heart of strategic decision making in businesses, whether they are huge multinationals or small family-run operations.”

All the information you need to improve all aspects of your business like customer experience and revenue generations are embedded in the data you already collect. Ignoring that intelligence and lying, to both yourself and your team, about why certain decisions are made will only hurt your reputation as a leader.


12. They Set Goals and Focus on Tasks They Believe in

On a related note, when it comes to setting goals and prioritizing different projects or tasks, the best tech leaders select issues they care about and pursue solutions they believe in.

When you break it down, taking the reins on an initiative you don’t feel strongly about is more than a little pointless. Whether the data isn’t there to back you up or a certain move goes against your gut instinct, belief in goals and the underlying process is an often overlooked ingredient to consistent team motivation.

By that same token, goals or projects that clash with a leader’s values or purpose as a tech entrepreneur will never be pursued with the same gusto as ones they and their team truly care about. As Margaret Thatcher once said, “don't follow the crowd, let the crowd follow you.”


13. They Stand For Legit Values, Not Empty Platitudes

Even the most pedestrian of internet users can distinguish legitimate values and clear-eyed organizational missions from empty, boilerplate platitudes.

What do I mean by empty platitudes? Often, they’re generic statements that any executive or company, regardless of what industry they operate in, could make. Everyone strives to be “dynamic,” “disruptive,” “dedicated,” and so on. The real question is how.

How will you get there? How will you, as a leader, instill the kind of behavior in your employees that create an unbeatable customer experience that everyone loves? Be specific, be inspiring, be unique, and never resort to milquetoast leadership speak. We’ve all heard it before, and frankly, the vast majority of people see right through it.


14. They Don’t Hold Employees to An (Excessive) Schedule

Assigning excessive workloads to your team and holding them to unrealistic productivity standards isn’t just poor management. It’s one of the main reasons professional burnout rates have skyrocketed.

According to both Gallup and the Mayo Clinic, unmanageable workloads lead to poor performance and elevated stress levels. As a result of being overworked and seeing no end in sight, staff members burn out, which can be extremely costly to even the biggest of corporations.

Here’s another truth that no manager wants to hear: Piling more work and pressure on your employees doesn’t keep them on their toes or motivated. In fact, it does the inverse. Untenable workloads and schedules without any upside lead to apathy instead of increased productivity.


15. They’re Not Afraid to Take Feedback, Even if it’s Harsh

Now we come to one of the thorniest of all leadership situations: being able to take even the harshest of feedback in stride.

Part of the reason that some managers and executives are allergic to truthful, hard-nosed criticism is that, as per HBR, what little feedback they receive isn’t helpful. Couple that with the serious side effects that can accompany poorly delivered negative feedback, and you’ve got a scenario most leaders avoid. But that doesn’t mean you should too.

While the truth can sometimes be the last thing entrepreneurs or CEOs want to hear, it’s always information that they need to hear. Success doesn’t happen in a vacuum and, if you don't ask for and take feedback seriously, you’re positioning yourself as part of the problem, not the solution.


16. They Don’t Weaponize Someone’s Side Hustles or Personal Life

Like it or not, we now live in a world where participating in the gig economy is pretty much the norm. Recent numbers reveal that American freelancers alone contributed $1.28 billion to their national economy. And, if growth stays stable, more than 50% of the US workforce will be ingrained in the gig economy by 2027

Why is this important to tech leaders? Well, it means the antiquated practice of holding someone’s side hustle against them (i.e.–all your professional drive must reside at OUR company) does more harm than good. What an employee does once they’re off the clock shouldn’t impact how they’re treated while they’re on the clock.

The same goes for a staffer’s personal life. Unless it’s affecting the quality of someone’s work, such as a substance abuse issue that spills over into their workplace, deriding an employee’s personal choices will only sour your relationship with them.


17. They Get Out of Their Talent’s Way

Finally, we return to the beginning of this discussion with perhaps the most golden of rules from the standout leaders across all business sectors: Get out of your talent’s way.

In her book “Bossypants,” SNL alum Tina Fey put it best when she said that, “in most cases being a good boss means hiring talented people and then getting out of their way.” It’s really that simple.

If you build up that trust from Day One and actually let your staff members do the work you hired them to do in the first place, you’ll be instilling the confidence and motivation that begets company loyalty. On top of that, they’ll bring new ideas to the table and organically create an innovative, collaborative environment that requires little to no policing.

These aren’t the only mistakes great tech leaders are able to avoid. There are plenty of other obstacles along the path to entrepreneurial success in a digital-first world, especially if managers and executives are deploying change management initiatives to streamline their organization’s daily operations.

Thankfully, there are always tips, tricks, and examples of how any leader can do their part to make any digital transformation push a positive one. To read more about you and your team can maximize that return on investment, click over to our blog!

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Originally published Dec 3, 2019 3:00:00 AM