Article
Is it time to upgrade your team?
August 13, 2020
Building on each other’s experience and expertise, teams can rise higher than a single individual can.

Surround Yourself with Knowledgeable and Experienced People
Effective leaders surround themselves with people who have technical and functional expertise. Like the cabinet of a president or prime minister or the military’s top level “joint chiefs of staff,” the best leaders create a powerhouse team of experts to advise and support their leadership. This doesn’t happen overnight; it requires you to continuously upgrade your team. Unfortunately, some of the early founding team members may not have the necessary skill and expertise to remain in their original role.
“The hardest thing to get right in every company isn’t the products but the people,” said John Chambers, former CEO of Cisco. So, it’s vital that the leader hire and empower a senior team that has expertise in key domains and then learn to value and listen to their views and utilize their insights.
Effective leaders need to augment their leadership style with people who complement their strengths and offset their weaknesses. To do this right, leaders must be honest and objective in assessing their limitations and stylistic tendencies.
“Lisa is a wonderful team-builder. We're lucky to have someone so adept at seeing each team member's skills, putting them to good use, and helping the team understand how best to work with each other.”
So it is critical to hire and empower people you can trust, who have experience and expertise you can learn from. Choose people with expertise in many different domains and let them lead those teams and functions. Select team members based on their technical, functional, problem-solving and interpersonal skills or on their potential for growth. They may come from varied backgrounds and have different styles but share a common set of values that make them fit in and enrich the culture of the team and the evolving organization.
TIP: Avoid hiring people you can control who will not challenge your point of view and may confirm your bias. Rather than thinking short-term and filling key slots with junior people who will be over their heads in a short time, hire people who are smarter and more experienced than you are and who can scale with the company. “The best leaders know that their employees know more than they do.” – Simon Sinek
It’s also best not to overdo hiring people just because they have degrees from prestigious schools and you assume, they have a high level of intelligence and lots of motivation. They may also have little experience and functional or domain knowledge. Without experience they may not have the framework to understand problems and won’t recognize patterns and errors that lead to serious mistakes and poor judgment. Experienced executives have models and pattern recognition to help them quickly spot problems and solutions rather than having to reinvent the wheel. Furthermore, don’t confuse personal ambition with achievement drive. Overly ambitious people are often poor team players.
One of my clients was growing rapidly and having great difficulty recruiting top technical talent. The recruiting organization had grown substantially but was not getting results and was having numerous internal and external problems. The CEO decided that his current VP of People (Human Resources) didn’t have the necessary skills to systematically manage and grow the recruiting team. He decided to move one of his executives from an operational position to head up the human resource organization because she was an outstanding project manager, a tough and disciplined taskmaster, and he hoped she would bring the structure, rigor and discipline that was necessary. The problem was that she had no HR experience and had poor people skills. It did not work out well, and within six months she was replaced by a seasoned HR executive. I’ve seen this story repeated many times.
Value the Contributions of all team members
To have a true “team” rather than just a collection of individuals, members need to value each other’s unique skills and contributions and appreciate the importance of each member’s role. As the leader, it is up to you to model this team spirit in your behavior and promote a team culture that exemplifies it.
How do you do this? When you show interest in a member’s activities and initiatives, openly express appreciation for the person’s efforts and achievements, it is obvious to everyone that the leader values that member’s contribution. Everyone is watching.
Many leaders tend to directly or indirectly show a preference for certain functions, teams, employee groups or areas of expertise. For example, in technical companies, the CEO often clearly values Engineering or Product over other functions. This results in the leader paying more attention to the views and recommendations of certain team members and listening more to their input in meetings. Whatever your background, personal preferences and predilections, try to be even-handed toward all functions and teams. In meetings, particularly those that involve strategic decision-making, it is important for the leader to include a wide variety of people, and actively draw out their ideas and opinions.
Clarify Roles and Responsibilities
Roles define individual responsibilities for successful operation of the team. Lack of role clarity is one of the causes of conflicts, confusion, and inefficiency on teams. Ideally, you want the team to function as an interdependent, coordinated unit whose members interact creatively and harmoniously.
Clearly defined roles promote efficiency. When the leader doesn’t make roles and responsibilities clear or designate who is responsible for and has ownership of specific projects and decisions, then power struggles and border skirmishes result. So if you are the leader, it’s important to define people’s roles or there will be battles over turf and authority, and chances are good that you will ultimately be called on to adjudicate!
Clear boundaries and assigned areas of authority are the key. For the team to function at maximum capacity, members need to understand not only their own, but also each team member’s roles and responsibilities. Consider creating an enhanced org chart that everyone can refer to, that defines the roles, responsibilities, deliverables, and decision authority of each team member. And be sure to update the chart as the organization grows and roles and responsibilities expand and shift.
In every company and team, there are both formal and informal roles. Formal roles involve designating who is responsible for doing what, sometimes accompanied by a title or a job description. On the other hand, informal roles are roles that people spontaneously take on, based on their personality, skills and style, and what problems need to be resolved.
For example, the question may arise, Who is going to be the person we go to when we have execution issues? Often there is someone on the team who is super organized and knows how to get things done, so this person becomes the go-to person for execution questions. Or there may be a person who has deep customer insights or knowledge of current technology trends or has their finger on the pulse of the morale of the engineering team. Often these informal roles can play a valuable part in improving the quality of understanding of problems or critical decisions.
Give High Powered Team Members Independence
Give team members autonomy – when they have earned it. Be sure to give team members the autonomy they want and need, particularly those who have demonstrated that they have good judgment and know what they are doing. “Barry does a great job of granting autonomy and at the same time making people feel like they are really part of a team, not just a worker”.
But be careful: some confident individuals may expect to have freedom and independent decision-making authority before they are actually ready and have demonstrated competence and good judgment. Their exaggerated self-confidence and personal ambition may cause them to overestimate their capabilities. They may not know what they don’t know. As the saying goes, “He was not always right but he was never in doubt.”
Discourage dependence. Other team members, who may be less experienced or less confident, will often overly rely on the leader to tell them what to do. This second type can become dependent, looking to management and leadership for guidance and direction even in small matters, and will have difficulty making the transition to independent decision making as the company grows. Discourage this kind of co-dependent relationship; it will eat up your time and will prevent followers from operating as true partners and leaders in their own right.
Over-controlling, narcissistic leaders don’t develop other powerful leaders, whom the organization needs in order to scale effectively. As much as possible, once people have demonstrated good judgment and their ability to get results, give them more independence and more decision-making authority. They need to know what is expected of them, but once they prove themselves, let talent find their own way to get results. Their mistakes can be learning opportunities and if you coach them properly, these need not be fatal mistakes. Micromanagement leads to decision bottlenecks, frustration, poor morale, and ultimately to executive turnover.
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Most startup founders are brilliant at innovation, disruption, and blazing new trails. They're visionaries, incredibly driven, and fiercely independent. Unfortunately, those same powerful traits often sabotage their ability to foster genuine collaboration—a critical ingredient in startup success. I've spent decades coaching founders, and one of the biggest blind spots I've observed is the gap between what founders naturally do well and what's required to create truly collaborative cultures. Understanding these tendencies—and knowing how to counter them—can mean the difference between startup stagnation and breakout growth. High Independence, Low Collaboration Founders thrive on independence. They love breaking rules, ignoring boundaries, and pushing limits. But independence can quickly morph into isolation. The very idea of slowing down to seek consensus or accommodate team input feels restrictive, even suffocating. Implications: This independent streak inadvertently sidelines team members, suppresses input, and reduces engagement. Talented people quickly learn their ideas don't matter, and teams become passive or defensive. Actions to Counter: Practice deliberately inclusive decision-making. Clearly define which decisions you'll make alone and where you'll solicit team input. Regularly check in to see if team members feel heard and involved. Dominance Isn’t Always Dominant Many founders naturally take a commanding stance. Their assertiveness, directness, and forcefulness can spark initial progress but, over time, it creates resistance. When team members feel steamrolled or fearful of speaking up, creativity vanishes. Implications: A dominant style shuts down communication, makes feedback difficult, and kills the very collaboration needed for sustained innovation. Actions to Counter: Make intentional space for quieter team members to speak. Foster psychological safety by modeling vulnerability and humility Balance assertiveness with curiosity—actively seek feedback rather than waiting for it. The Curse of Poor Delegation Delegation isn't just handing off tasks—it's handing off trust. But founders notoriously struggle with this, often believing only they can execute properly. Every task not delegated reinforces the message that the team isn’t capable. Implications: Poor delegation creates bottlenecks, slows execution, and demoralizes talented employees who feel undervalued and micromanaged. Actions to Counter: Start small by delegating lower-risk tasks clearly and thoroughly. Regularly check your impulses to micromanage; remind yourself why you hired capable people. Invest in mentoring and coaching rather than controlling. Communication Breakdown Founders are famously impatient. They think fast, act fast, and often communicate quickly or incompletely. What seems obvious to them might be totally unclear to their team. 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Conflict Avoidance (or Aggression) Many founders fall into two extreme camps: conflict avoiders or conflict initiators. Both extremes are deadly to collaboration. Avoiding conflict leaves critical issues unresolved. Aggressive conflict handling creates resentment and fear. Implications: Poorly managed conflict erodes team cohesion, undermines trust, and can spiral into prolonged dysfunction. Actions to Counter: Establish clear, structured conflict resolution processes. Practice direct yet respectful conflict conversations. Use neutral facilitation for emotionally charged discussions. Systems Thinking vs. Reactive Planning Startups prize agility and adaptability. But too much short-term thinking neglects the processes and structures that sustain collaboration. Without clear systems, teams fall into chaos. Implications: Reactive planning leads to burnout, inefficiency, and frustration as team members constantly fight fires rather than building strategically. 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Start today by picking just one area and committing to small, consistent improvements. Your team and your startup—will thank you.