Winning Well — Book Review and Summary

I have been rather busy this past month, mostly due to business travel and offshore duties. So, book time has been reduced significantly. However, making time to “Winning Well” was worth it. It is a practical book for leadership, which also works for aspiring leaders as well.


The book prescribes giving equal weight to four pillars of sound leadership

  1. Confidence
  2. Humility
  3. Results
  4. Relationship

This aims to create a positive environment and generates long-term results while energizing your subordinate, recognizing their achievements and fostering their sense of fulfilment.

Among key points from the book include the needs for managers to specify their expectations, provide resources, reinforce priorities and acknowledge success. Also, need to be clear about the decision-making process and who has the final word.

Don’t micromanage but rather delegate results so workers can improvise and innovate.

When giving out praises, make sure to make it in a focused recognition style. Meaning, recognize success with praise that is pertinent, detailed and “meaningful”.

The purpose of meetings is to decide what must happen, who’s responsible for it, what the deadlines are and how the team will know it’s done.

Make use of the “INSPIRE” framework to guide evaluative conversations with individual employees about accountability, performance and productive behaviours. In case you are wondering, the term “
INSPIRE are acronyms for – Initiate, Notice, Specific Support, Probe, Invite, Review, and Enforce.


However, creating a work environment which can unleash and develop employees internal motivations are crucial, and can also be challenging. Everything needs to be in place, from the talent pools to the resource availability. This reminds me of Ray Dalio’s The Principle, which suggest, getting rid of those who didn’t fit the team is the best for all involves. Yet, most managers nowadays, can’t simply wield the sword, basically due to lack of autonomy or again, talent pools or resources.

End of the day, we must make do with what available to us.

However, another principle from Ray Dalio’s masterpiece which I truly love, brutal honesty and transparency. Which would greatly encourage honest feedback, encourage vigorous debate.

Winning well by striking the right balance.

  • Clearly, describe the work your team needs to produce and how that goal fits your organization’s objectives;
  • Develop a straightforward plan for achieving the results you want;
  • Outline the actions your staff needs to undertake to bring that plan to fruition.

Working toward mutual goals requires collaborating, functioning as a team and knowing that you’re all on the same quest. Hold yourself and your team accountable for each shared commitment.


Four Types of Managers

Managers generally fall into four categories:

  1. Users
    • Treat people as vehicles for getting what they want.
    • Focus on short-term results generated under the fear of reprisal.
    • Users and their workers don’t trust each other.
    • Users become work-police who don’t believe their employees will fulfil their responsibilities without being forced.
  2. Pleasers
    • They value being liked more than anything else.
    • While many employees do like them, but high-performers resent them because they don’t prioritize productivity and results.
  3. Gamers
    • They play office politics to increase their status and get ahead.
    • They sacrifice relationships to prioritize their own agendas instead of the firm’s goals.
  4. Winning Well managers
    • They focus on long-term, shared goals.
    • They develop healthy work relationships, clarify expectations, and support their employees’ growth and success.
    • Their team members feel less stress, are more productive, work autonomously and efficiently, and are happier overall.

“High performers hate nothing more than watching their poor-performing, soul-sucking teammates drag down results.”

Great managers use metrics to reinforce the behaviours they want employees to follow, but they don’t live or die by the numbers. They understand that managing isn’t a zero-sum game; people don’t need to sacrifice happiness to succeed or give up good relationships to be productive.

Winning Well’s foundational principles are not options; all four elements – confidence and humility, and results and relationships should be present.


Winning well by setting your team for success

Clear communicating, specific expectations. Often, people ran off track when they don’t understand what you expect from them.

“Busy doesn’t mean productive. Be intentional with time to restore your productivity.”

You also can’t assume your team members have the necessary skills to meet your expectations. Provide training, resources and guidance to set them up to meet their goals. Reinforce your priorities frequently and in different ways to keep your most important objectives top-of-mind.

When your team members achieve a goal, acknowledge their work and celebrate. If they fall short, hold them accountable, but not by placing blame. Remind them of their commitments; ask what slowing their progress, and brainstorm ways for them to succeed next time.

“When you tell a competent person how to do something she already knows how to do, it’s insulting and demeaning, and it degrades trust.”

  • Schedule meetings only when they’re valuable to everyone.
  • Invite the smallest possible number of people to make decisions or devise action plans.
  • Focus on “building relationships or achieving results.” Relationship-building meetings identify inarticulate problems, celebrate achievements or provide opportunities to share ideas.
  • Results-oriented meetings move your group closer to its goals by generating relevant action.
  • Use meetings as “commitment creators.”
  • The purpose of meetings is to decide what must happen, who is responsible for it, what the deadline is and how the team will know it’s done.

Decision Making

People want to be included in deliberations about the work within their purview. They’re more likely to make peace with a decision when they’re involved in the discussions that shape it, even if they don’t wholeheartedly agree.

In order to make informed choices, managers should seek employee input and buy-in during the decision-making process. To avoid engendering frustration, be clear about how the process will work and who has the final word.

“Nothing energizes an employee quite like the feeling that he’s just jumped out of an airplane and discovered he has a parachute he didn’t even know existed.”

Business decisions call for discussing both methods and goals. You can reach decisions in four ways:

  1. Have one person make the final call after receiving team input,
  2. Initiate group discussion followed by a vote,
  3. Reach consensus by discussing the topic until everyone agrees on a way forward, or
  4. Flip a coin if the options are equal and the choice doesn’t have much impact, like the decision about where your team will have lunch.

Winning well by looking to I.N.S.P.I.R.E.

Failing to hold people accountable for undermines your reputation and credibility. Set high expectations, and help your team members live up to them. Hold “accountability conversations” during a one-on-one dialogue to examine performance issues and identify more productive behaviours.

Guide these conversations using the INSPIRE method:

  • Initiate – Invite the person involved to talk. Set an appointment time.
  • Notice – Respectfully communicate your concern about the employee’s behaviour.
  • Specific support – Clearly explain what caused your concern.
  • Probe – Solicit input; let the employee tell his or her side of the story.
  • Invite – Invite the employee to present workable solutions.
  • Review – Summarize the conversation while checking for understanding.
  • Enforce – Reiterate the reasons why you want to see a change of behaviour. Express confidence in the employee’s ability to follow through.

“When expectations are foggy, your people will lose focus and put their energy into other activities that make more sense to them.”

“Expect more, and watch your people’s energy lift as they rise to the challenge.”

Telling competent people how to do every aspect of their jobs demeans them. Be clear about schedules and deadlines to build in accountability, and be specific about assignments, but then let people figure out the best way to meet your expectations. For complex or long-term projects, arrange for regular status updates. Regular shouldn’t be too frequent.

Winning Well on Motivation, Confidence and Trust

Most leaders believe they’re responsible for motivating their employees. However, motivation comes from within each person. Consider various ways to create a working environment that cultivates motivation.

Provide opportunities for them to grow into new roles. Trust your employee to rise to fresh challenges. Micromanaging hurt trust between managers and employees. Demonstrate trust by setting ambitious goals, showing your belief in the team’s ability and collaborating on processes.


“Focusing on results exclusively may improve outcomes for a time while also burning out employees, increasing apathy and killing morale.”

  • Encourage problem solving and innovation by showing employees exploring new ideas is safe.
  • Recognize effort, not just the outcomes.
  • Trying a new approach doesn’t always work, but taking a risk is courageous.
  • Offer to provide training, tools and equipment.
  • Help people navigate any impediments to their personal success. Instead of jumping in with solutions, ask questions that enable team members to solve the problems they encounter.
  • If someone says, “I don’t know,” counter with the “magic” question, “What might you do if you did know?” People won’t stay motivated or productive if they don’t have a clear understanding of how their work connects to the organization’s mission.
  • They need to know why their results matters. Re-evaluate or eliminate tasks that don’t contribute to individual, team or company goals.

Feedback and Follow Through

“People in positions of power often sabotage themselves and create environments where no one will tell them the truth – often difficult truths about themselves.”

If you want employees to feel comfortable giving you input, suggestions and feedback, encourage vigorous debate. Thank people for bringing issues to your attention. Respond to ideas, even if you don’t find them feasible. Listen to other people’s contributions without becoming defensive. Cherish your truth-tellers, the people you trust to speak their minds.

If you’re feeling frustrated that your subordinates aren’t taking direction or following up on their goals, determine whether you have articulated your vision in a way that they can understand.

Are you issuing orders, or are you explaining expectations and why they matter? Remember, If you’ve communicated something once, you haven’t communicated.


Praise and Laughter

Taking a playful approach sometimes relieves stress and tension and frees people to explore their creativity.

“Sometimes you have to take action with the best information you have and move your team forward.”

“Winning doesn’t mean you reach some imaginary state of perfection. Winning means that you and your people succeed at doing what you’re there to do.”

Encouragement must be sincere, pertinent, detailed and meaningful. Mispronouncing the staffer’s name or making some other careless mistake negates the value of your praise. Acknowledge the activities that contributed to a team member’s goals. Be specific. Tailor your praise to resonate with the recipient.

Read Winning Well



Author: Muhamad Aarif

A notorious book addict by night and an oil and gas executive by day. As Mark Twain said, "The man who doesn't read good books has no advantage over the man who can't read them." So, read, read, and read some more.

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