It’s Time for a Frank Conversation About Leadership

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Being a Leader is a Serious Job

More than ever, today’s global political turmoil underscores the importance of leadership. Inspired, trustworthy, ethical, strategic leaders are critical to ensuring a country’s growth and stability. Not surprisingly, the same valued leadership qualities are critical in ScaleUp companies too.

The reality is, many leaders are not up to the challenge, building weak company cultures that lack strong values, with little sense of mission or purpose. In an Inc. survey, 75% of employees said that “their boss is the worst and most stressful part of their job” and 65% of employees said they would take a new boss over a pay raise. 

We need good role models

The tech industry has many examples of ineffective leaders: those who’ve had scandalous affairs with employees, who tolerate – and sometimes encourage – toxic cultures, who engage in obfuscation or fraud. These are newsworthy and should be called out. What’s less discussed is the high number of leaders who don’t have a strategy that they execute on and who don’t know how to manage teams and hold them accountable. The latter category of leaders is far more ubiquitous and equally as damaging to employee and shareholder value, along with hindering hope and potential. A Forbes article eloquently distills the telltale signs of bad leaders. I’ve grouped these into errors of omission (actions that are not taken), and commission (actions that are deliberately taken).

Actions of omission by leaders. They:

  • Don’t communicate a clear vision for the future
  • Fail to inspire employees
  • Fail to communicate clear expectations
  • Fail to recognize and give credit to employees for accomplishments and efforts
  • Accept mediocrity rather than motivating excellence
  • Lack enthusiasm and passion for the work the company is doing
  • Are insecure in themselves which often leads to mean, paranoid, vindictive behavior 

Actions of commission by leaders. They:

  • Selectively communicate with only a few people, leaving others to feel devalued and left out
  • Pick and choose who they will value rather than seeing the team as a whole
  • Reward based on brown nosing rather than performance and impact
  • Attack people, rather than attacking performance
  • Make decisions off rumors (or gut feel) rather than taking time to gather all the facts
  • Place blame on others rather than owning mistakes themselves
  • Don’t follow through on their commitments to employees

As you read the list above, it’s clear that many of the acts of omission can be solved with basic manager training. Often employees rise through the managerial ranks based on their individual performance in their role, and the job of managing the team is an afterthought. What executives need to remember is that being a manager is a full time, and serious job of its own; appointed leaders need to be given the space and training to dedicate time to management. Providing leaders with a framework for how to be good leaders may allay some of these leadership challenges, specifically things like setting expectations, regularly communicating to teams, implementing performance and feedback processes.

The acts of commission can also be avoided with training and awareness, but many of these common behaviors highlight that some people are not cut out to be leaders. We place a high premium on leadership in our society, but not everyone needs to be a leader. Being a leader is a deliberate choice that requires taking responsibility for outcomes and being accountable for team actions. It also involves making tough decisions and owning the consequences. A leader is on the line, and in the spotlight. If an executive can’t make these types of commitments, or be a ‘conscious leader’ who brings their entire self into the leadership position, then an organization should not put them into a leadership role. 

The irony in the term ‘leader’ is that while, by definition, it places the individual at the front, being a leader actually requires putting others first. Removing roadblocks that may slow down momentum and taking satisfaction from watching their team charge ahead. A leader’s work doesn’t focus on “yourself” but on the people being led, the customers being served and the organization’s goals and needs. A leader’s obligation is to put these interests ahead of their own. If a person can’t, or doesn’t want to do this, they shouldn’t be in a leadership role.

Choose leaders who can commit to leadership principles

In many high-growth software companies, leaders become heads of teams, or are promoted to Vice President, or C-level titles by virtue of being among the first people in the company. In the companies that Insight Partners invests in, tenure, knowing the founding team (or being part of it), and institutional knowledge are sometimes the best indicators of why someone is in a leadership position. However, this way of selecting leaders, more often than not, produces leadership that implements the acts of omission and commission mentioned above.

Instead, companies need to select leaders who will sign up to a code of conduct. In his book, The Leadership Contract, Vince Molinaro notes that many leaders step into leadership roles without thinking about what it means, and they grow to be ambivalent about their responsibilities. Molinaro suggests that companies follow four strategies to develop a cadre of good leaders. He calls this the “leadership contract.”

  1. Prioritize accountability in leader’s performance reviews. Companies should ensure leadership are held accountable.
  2. Write a contract for leaders. Leaders should adhere to a “social” contract that lays out leadership expectations. These include values, ethics, as well as hard numbers and goals. When someone assumes a new leadership role, they should know what they’re signing up to. By making this explicit, people can make an active choice to assume a leadership role or not.  Leadership should be a choice, not something that people “fall into” by virtue of tenure. 
  3. Provide “tough” feedback. Leaders need to not only take, but be able to provide feedback to their teams, which includes engaging in difficult conversations and not letting poor performers get away with their mediocrity. By providing honest feedback, leaders send a signal to everyone that performance is expected, and that people are given an opportunity to improve.
  4. Bring leaders together. When leaders connect with each other, and talk to one another, a strong culture of communication and support develops. Strong relationships between leaders will ensure cross-company learning and avoid departmental silos. It will also help leaders be better at their jobs through observing and copying the good behaviors they see in their colleagues.
  5. If taken seriously, being a leader is challenging. It can also be tremendously rewarding, particularly when employees develop and grow personally, and when individual, team and company goals are accomplished. Great leaders can be made, they don’t have to be born. As Insight’s portfolio companies ScaleUp, a strong leadership team with a vision, strategy, bias towards action and culture of accountability is the difference between companies that grow to be large, vibrant, market leaders, and those that don’t. 

As founders and CEOs, it’s incumbent upon you, the “first among equals” to lead teams. One of the best ways you can do this is to grow strong leaders beneath you, at every level of the company. Select and nurture high performers who want to be leaders and coach them using the four steps above. 

The world needs great leaders. Leaders who are not only inspirational, but aspirational for people rising around them. In a world in which change is constant, our society needs leaders who understand what they’re being asked to do, and who sign up to be accountable, ethical and inspiring. Leaders who understand that leadership is difficult, and a serious job. As John Maxwell, leadership author said, “The single biggest way to impact an organization is to focus on leadership development. There is almost no limit to the potential of an organization that recruits good people, raises them up as leaders and continually develops them.”

  • Hilary Gosher

    Hilary Gosher, Managing Director

    Hilary Gosher is a Managing Director at Insight Partners, and a growth zealot. She leads Insight Onsite, the firm’s operators and growth experts who accelerate scale at portfolio companies. Hilary founded this team and has worked with more than 200 software companies. She leads Insight's due diligence, software Centers of Excellence…