9 Leadership Paradoxes That Can Make or Break Your Career
Tips and strategies to navigate them
✨
Leadership is never black or white.
It’s a constant dance in the grey—balancing decisions that seem contradictory yet are both essential.
Should you lead with authority or humility? Push for results or prioritize relationships? These aren’t just dilemmas; they’re paradoxes every leader faces.
In this article, I’ll unpack nine paradoxes that define the leadership journey. These are not abstract concepts, but real tensions I have grappled with daily, and I’m sure you do as well.
And while each paradox seems counterintuitive at first, they hold the keys to building stronger teams, driving change, and leading with impact. Ultimately, how you handle these paradoxes can either make or break your career.
Ready to dive in? Let’s go!
Confident… or Humble?
Imagine you are a CEO, and during a company crisis, you confidently present a plan to reassure stakeholders about how you plan to recover from the crisis.
The stakeholders are satisfied with the explanation, and they reaffirm their support of your business.
However, when you have a meeting with your leadership team, you admit that you don’t have all the answers, and you demonstrate your vulnerability and humility.
Your leadership team appreciates your authenticity, and actively engages in and contributes to the discussion.
Takeaway: Confidence is necessary to maintain morale and direction toward the goals. However, humility and authenticity are essential to solving tough problems in order to move towards your goals. In The Five Leadership Secrets You’re Not Supposed To Know we discussed how leadership is more about people than strategy, and how should be putting your team first to balance humility with confidence.
Strategic… or Tactical?
Imagine you are a startup founder, and you are passionate about your vision and strategy for your company.
You can’t stop talking about revolutionizing the industry, and the infinite potential your business has.
Simultaneously, you work with your product teams to build the product, get it tested by your current early adopters, and continue to iterate on it. You work with your finance team to make sure you can keep the company afloat, while keeping a close eye on the expenses.
Takeaway: Leaders should have a grand vision and strategy to inspire their teams and stakeholders. At the same time, they should not lose sight of what is necessary at the moment — the tactics — to avoid disappointment. In Mind Boxing: How Leaders (Should) Spend Their Time we discussed an approach that you can use be intentional about how you allocate your time across strategy and tactics.
Decisive… or Flexible?
Imagine you are a project manager responsible for a high-profile project that is falling behind schedule.
In the interest of the project, you drive towards decisive actions to keep the project moving in the right direction.
Later, you receive new information from the team working on the project, and that has the potential to change the scope and viability of the project.
You cannot afford to ignore this, and you demonstrate flexibility by adjusting the plan and continue to iterate and adapt as needed.
Takeaway: Decisiveness is important for progress, and to avoid stalling or going in loops. At the same time, flexibility and agility are important to ensure you are adapting to environment to optimize execution. In The Daily Rituals of Highly Effective Leaders we discussed how great leaders start their day with clarity and support their team by listening to their concerns.
Resilient… or Vulnerable?
Imagine you are a military leader. Your role demands extraordinary strength, endurance, and resilience to handle difficult missions.
You make tough decisions that impact not just the lives of your own team, but your mission or your country.
At the same time, you need to know your team members as humans, not just as resources that can be expended.
You need to understand their struggles, their strengths and weaknesses. You need to be vulnerable and authentic in front of them, and share your own struggles to build trust.
Takeaway: Resilience is important as it builds confidence, and enables you to handle difficult situations as a leader. At the same time, you need to be open to being vulnerable to build deeper connections and trust with your stakeholders. In 5 Quick and Easy Ways to Earn Respect As A Leader we discussed how leaders, no matter how tough they might be, will only earn respect from their team members when show care and empathy towards them.
Enjoying the read? Subscribe to The Good Boss to get free articles like this every week.
Empathetic… or Tough?
Imagine you are the principal at a reputed school in your district. Recently, you have rolled out a new policy at your school that will help the school emerge among the top schools in the country.
However, your teaching staff has several concerns, and you show empathy by listening to their concerns about the new policy. You make sure they feel heard.
At the same time, you know that the policy needs to stay for the long-term success of the school. So, despite understanding the concerns of the teachers, you re-iterate the need for them to champion the policy, and demonstrate toughness in your resolve to uphold the policy.
Takeaway: As a leader, you should empathize with your teams and make sure they feel heard. At the same time, you may need to be tough and play bad cop at times, and stand behind what’s right, even if that means enforcing an unpopular policy. In The Strategic Leader's Dilemma: Immediate Results or Future Vision? we discussed a framework you can use to strike the right balance between now vs the future.
Controlling… or Delegating?
Imagine you are the head of marketing at your company, and you have a new marketing campaign to roll out for a brand new product.
You delegate the campaign responsibilities to your team as you want to encourage creativity and out-of-the-box thinking. This will ensure that the best ideas surface to the top to maximize chances of a successful campaign.
However, your campaign needs to be rolled out in four weeks, and you set clear deadlines — including internal check-ins — that your team needs to meet and provide regular progress updates.
You do this to ensure that the team remains on track with the timeline, and you also get the chance to review progress and provide feedback to the team on a regular basis.
Takeaway: As a leader, you should empower your teams by delegating work that they can handle better and with greater freedom. However, while doing that, you shouldn’t let go completely, and exercise control by making sure you hold them accountable to the ultimate outcomes and expected quality and timeline expectations. In 15 Cognitive Traps That Are Sabotaging Your Leadership we discussed how Illusion of Control can be a trap that managers need to be mindful of as they plan and execute projects.
Energetic… or Calm?
Imagine you have been asked to lead a new project that has high visibility, while an extremely tight timeline.
You are excited, and energized with this opportunity, and start rallying your team around this new project. Your enthusiasm is palpable, and rubs off positively on your team’s productivity.
A few weeks in, the project runs into major roadblocks, including a major flaw in your design that sets you back by more than two months.
However, you hold your nerves and remain calm when working with your team to work through this situation. You team needs the assurance that everything is under control, and the last thing you want to do is send out panic waves.
Takeaway: As a leader, your team looks up to you for energy and motivation. The more energy and enthusiasm you exude, the more energized your team will feel. However, in times of crisis, it is important for you to keep a check on your negative energy. You should stay calm and composed, and provide the necessary assurance and support to your team to work through the situation. In 6 Simple Strategies To Navigate Office Politics Like a Pro we discussed the importance of being self-aware and knowing your blind spots, so you can handle situations tough situations with the right composure.
Discrete… or Transparent?
Imagine you are a senior executive at a reputed company that has millions of customers. You are answerable to the board of directors, and your entire organization looks up to you for direction.
You understand very well that one of the essence of building trust in your organization is transparency. You strive to keep your teams informed about updates related to the business, the roadmap and the company direction from time to time.
You make sure they feel heard, and do not feel left out in the dark.
However, in your leadership position you are also privy to sensitive information — from legal to financial data — that you need to hanlde with discretion and utmost confidence.
By doing this, you are not only protecting the interests of the company, you are also upholding your own integrity.
Takeaway: It is important for leaders to be transparent to build trust, but they need to be careful about what is shared and how. Discretion is also very important, as it protects sensitive information, and the strategic interests, while upholding their integrity. In The 3 Stages of Communication in Leadership we discussed a structured approach to communication in leadership.
Personal… or Professional?
This is a popular conundrum faced by managers, especially first-time managers.
How close can or should you get with your team members?
As a leader, you want to encourage a sense of belonging in your team by celebrating personal milestones of your team members — such as birthdays or family achievements. This helps to add a more human touch to your support and recognition of the team members beyond just their impact on the business.
At the same time, you must maintain professional boundaries and cannot undermine the professional contributions by your team members. You must ensure you are evaluating performance and rewarding team members fairly and objectively.
Takeaway: Building personal connections can help to foster a supportive environment that recognizes team members as human. At the same time, you must draw the professional boundaries, and be ruthlessly objective when it comes to performance evaluation based on business objectives and results. In Maslow's Hierarchy of Needs in Leadership we discussed how you can understand the needs of your team, and align those with your business priorities.
In Summary: 9 Leadership Paradoxes That Can Make or Break Your Career
As a leader, you often find yourself in tricky situations and face contradictions where you are unsure of what position you should hold.
In this issue, we discussed nine leadership paradoxes that every leader faces, and how they can handle them when faced with them.
Confident… or Humble? Confidence is necessary to maintain morale, while humility is essential to solving tough problems together.
Strategic… or Tactical? Having a vision and strategy inspires teams, while not losing sight of the tactics ensures accountability and execution towards the goals.
Decisive… or Flexible? Decisiveness is important for progress, while flexibility and agility are important to ensure you stay relevant.
Resilient… or Vulnerable? Resilience is important to handle difficult situations as a leader, while vulnerability helps to build deeper connections and trust with your stakeholders.
Empathetic… or Tough? You should empathize with your teams to ensure they feel heard, but you should also stand tough behind what’s right even if that means playing bad cop.
Controlling… or Delegating? Delegating work to teams can empower them to do better, but you should exercise control and ensure accountability as you do so.
Energetic… or Calm? Leaders should exude energy and enthusiasm to inspire their teams, while making sure they remain calm and composed in times of crisis.
Discrete… or Transparent? Leaders should strive to be transparent to build trust, but be discrete with sensitive or privileged information to uphold their integrity.
Personal… or Professional? Building personal connections can help to foster a supportive environment, but you must draw the professional boundaries to ensure fair and objective performance evaluations.
The reality is that leaders need to assess the situation, and adjust their stand based on the circumstances. In fact, on closer inspection, you will find that these traits are not contradictory at all, which is why they are really just paradoxes.
The more you are able to recognize them, the better you will handle them.
How many of these are you able to relate to? Have you ever found yourself caught up in these paradoxes? Share your thoughts in the comments below! 👇
You might like these other related articles
The Ultimate Leadership Toolkit Bundle 🛠️
Ready to take your leadership to a whole new level? Unlock the full power of the best leadership frameworks and tools with The Ultimate Leadership Toolkit Bundle! From application guides to mind-maps to posters to worksheets and much more - this is your ultimate leadership resource!
👉🏼 Grab your copy of the bundle
🎁 Paid subscribers to The Good Boss enjoy FREE access to the bundle! (worth $210+) Not a paid member? You can upgrade here.
👋🏻 Let’s stay in touch - connect with me on LinkedIn.
PS: If you’re enjoying The Good Boss, will you take 2 seconds and hit the ❤️ button and share/restack 🔁 it with others who might find it helpful? It goes a long way in helping me grow the newsletter. Thank you!
If you are not already, subscribe to The Good Boss for free articles like this every week.
As you mention, leadership is not black or white. The ability to adapt is probably our biggest asset as a leader. I enjoyed learning about those paradoxes and their leadership implications!