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Decide and Conquer- Book review

1 June 2024
Dr. Moria Levy
book cover

The book Decide and Conquer: 44 Decisions That Will Make or Break David Siegel, the CEO of MeetUp, wrote All Leaders. It chronicles his story, starting with his offer to lead the company and the rollercoaster ride he experienced in this role. The book is organized by periods of activity. Still, I chose to summarize it according to the nature of the decisions, grouping some based on the assumption that managers reading the book will need the knowledge, not necessarily always in the order it occurred in Siegel's life story. The summary hints at but does not focus on the big drama of MeetUp's acquisition by WeWork, then bringing in David Siegel to lead the company, shortly after that, the parent company's decision to sell the company, and the impact of the coronavirus on the company whose product's purpose was to hold live, in-person meetings. We will not describe how the drama unfolds and ends here to leave you in suspense when reading the entire book.

Every CEO and leader experience their own life story, but the challenges, it appears, are similar and shared. There is something to learn, and it is good to know, precisely in a role that always gives a feeling of loneliness, that you are not alone.

And a spoiler: there are 45 decisions. We simply start with decision number 0.

Bottom line: highly recommended book!

Main points:

  • Basic principles

Decisions in different contexts:

  • The company

  • Relationship with the parent company

  • Relationship with the company's managers

  • Relationship with employees

  • Relationship with yourself!

Appendix: List of challenges and decisions.

Basic Principles

Here is a list of fundamental principles that guided Siegel's approach to making various decisions.

Every CEO needs to hold such a list of their own, defining them as a person and their leadership style as a CEO.

The application of these principles runs as a common thread throughout the book, as Siegel describes the various decisions he made:


Kindness is not just sympathy or empathy; it treats people humanely and minimizes pain.

Example: When Siegel had to downsize the company, he helped many find job opportunities at other companies.


Confidence is not arrogance. Being self-confident allows you to live with rejection and keep trying. It will enable you to give others the feeling that it is worthwhile to listen to you. Remember, management does not mean democratic management.

Example: In job interviews, conversations with employees, and conversations with investors.


Dare to ask, dare to demand, dare to move forward.

Even when it is clear that not all conditions are met, we will not always succeed - but it is worth trying.

Example: When looking for a new investor for the company, the CEO approaches many investors in the relevant network, even if they do not seem suitable; when there is a serious investor, it is suitable for the CEO to look out for themselves.

Expand Options

Striving to expand opportunities is a way to expand successes; there is never someone perfect for every need, and developing options is a meaningful basis for increasing the chances of winning.

Example: When Siegel faced two options for acquiring the company, and neither succeeded or was successful enough, he did not give up; he sought and created another option.

Long-term Picture

Even when faced with short-term challenges or opportunities, we prefer to make the right decision for the long term, as much as we can afford.

Example: Developing values that will form the basis of the organizational culture is essential to remain long-term.


Be honest and truthful with others and yourself, live in transparency (like in an aquarium), and do not use "laundered" terms. Sometimes, it requires some cruelty, but it is correct.

Example: Layoffs are not a "reorganization"; acquiring a company is not a "merger."

Example: Demonstrating honesty in expectations and performance towards the parent company.


Don't wait - make decisions immediately.

Example: The author talks about one night when he sent out 2,000 emails looking for a job.

Example: Replacing the management team that the CEO does not trust immediately upon taking office.


Make pragmatic decisions, even if they are not ideal.

Example: Taking a less good job when you need to support your family.

Example: Not relying on board promises when it is clear to the CEO that there is no reason for them to hold that position for long.

What is Right for the Business

Prioritize the good of the organization, the good of the employees, and the good of the managers over the good of the CEO.

Example: Consider stepping down as CEO if that is what is currently suitable for the organization.

Example: Prioritize what is suitable for the company over what is good for employees.

Work for Them, and They'll Work for You

Find ways to serve the employees and their needs.

Example: When Siegel had to downsize the company, he helped many find job opportunities at other companies.

Be Surprised Only from Being Surprised

There will be surprises; expect them, and don't dwell too much on "why didn't I know?" but simply... act.

Example: COVID.

Example: You should not be surprised if the parent company wants to sell the company shortly after the acquisition, even if nothing has changed in the primary conditions and if there has been an improvement.

Decisions - The Company

Acknowledging reality, even if it is difficult

A sober understanding of reality, even if it is difficult. This is true when entering the role when what you expect is not what is happening, but it is also true later when we can become entrenched in our conceptions and expectations (author's note).

Acknowledging reality is the first step in preventing a crash to the ground.

In Siegel's case, he quickly understood that while a company is supposed to balance the good of the company, customers, and employees (with that also being the order of priority when there is a conflict), in the company he received, the good of the employees was placed first, creating a situation that caused severe harm to the company.

Formulating a company strategy

Formulating a changing strategy, depending on the period:

  • Formulating an initial strategy that creates a new direction for the company needs to be (almost) immediate. The implication is speed at the expense of completeness. In the coming years, there will be opportunities for improvement.

  • A stabilization strategy is better partial, less data-driven, and even with some mistakes, as long as it is defined in the right direction and released on time. It is permissible and advisable to work with an iterative strategy. It is advisable to be ambitious but realistic. In any case, strive for an honest company as soon as possible, with a path to profitability and survival capability.

  • A growth strategy. Future-oriented. Aligned with the company's core values and focused on only a few narrow directions that could lead to success. Many times, companies fail due to a lack of focus.

  • Changing the strategy: It is right to make a significant change in the direction of activity of the company you manage when you lose alignment with the vision. Seigel shares the loss of MeetUp's vision due to the coronavirus and their ability to update the purpose in a way that put the company back on its feet (from physical meetings to virtual meetings).

    Often, it is not possible to predict the future. You have to act while looking and orienting towards the purpose.

    Principles for changing direction in the right way:

    • Leave a specific component unchanged. Do not change the company's mission.

    • Support the change with best practices. Communicate.

    • Understand what is happening in the overall ecosystem in which the company operates.

    • Focus on the future as well, not just the present.

    • Rely on data.

    • Look for new customers and new sources of revenue.

It will not always be easy to know if you have taken the right direction, but it is part of the CEO's role to ask the questions repeatedly. The very decision is not a complete stop but only the beginning.

In any case, to create a strategic plan that is inspiring but achievable, focused, flexible, realistic, and ambitious at the same time, it is advisable to examine the company's past. Even if we do not repeat history, there is much to learn.

Dealing with crises

  • When there is a crisis, being patient before rushing to make changes is right. It is not right to allow tension and pressure to influence decisions.

  • When there are no good options, it is right to act to create an additional option. If not, withdraw and hope for such an opportunity to arise.

Organizational Culture

Organizational culture aims to build employee behaviors that provide an advantage relative to competitors.

It is recommended that the values underlying the culture be developed with the employees by involving them in the process.

The values that MeetUp designed indeed remained unchanged after the building process (at least until the book was written), and they include:

  1. Trust and transparency

  2. Impact focus

  3. Openness to change

  4. Initiative

  5. Elevating people

  6. Integrity-driven leadership

Decisions - Relationship with the Parent Company

Realistic Reciprocal Relationships

Understanding that even if the acquisition process is called a "merger," it is not symmetrical.

Define success realistically vis-à-vis the parent company and not beyond that. There are usually excessive expectations. Base your recommendations, as well as your subsequent successes, on data.

Prioritizing the Needs of Your Company

When the needs of the parent company that owns your company conflict with your company's needs, it is always right to prioritize them.

Organizational Cultural Separation

There will always be a gap between a company's current culture and the company that acquired it.

In any case, even when changing the organizational culture, the needs and culture of the parent company are not always ideal compared to those of the company you are leading.

Siegel has no hesitation. He recommends maintaining an independent organizational culture rather than trying to connect with the parent company.

Owners You Are Not Aligned With

  • When there are owners who are very vocal and volatile in their behavior (like his famous owner of WeWork) - it is better to ignore them and avoid meeting with them as much as possible. No matter how important the CEO deems maintaining a solid relationship with the owners, this is not the best tactic for a highly volatile person.

  • When a significant gap arises between the goals the owner wants to achieve through the company and the goals of the CEO, it is right to part ways and leave.

  • Practical, Long-Term Analysis Regarding Owners' Statements About Your Company

Even if the parent company claims that it does not care about your losses, or when it comes to financial aspects, you should always think based on data and consider what they would reasonably feel about you from a practical and long-term perspective. In the case of Siegel, the owner above him insisted on revenue projections of one billion dollars, which was not feasible, and he was unwilling to hear any other assessment. Inevitably, Siegel [provided him with this assessment, but for all other board members, he was careful to present a realistic future scenario and, in any case, did not rely on their agreement to the current losses.

Dealing with Your Parent Company's Desire to Sell the Company You Lead

  • If the parent company announces that it wants to sell the company you lead, it is advisable to stop, take a deep breath, and look at the big picture. Such a picture will provide additional details that will help better deal with the news regarding the company: required time, desired return, nature of the buyer, urgencies, and more.

  • It is advisable to take responsibility for the sales process, dare, and even play the "bad guy" role. Do not go with the flow; instead, tilt it or be active in creating the process that suits you, even if the price is a personal risk. In Seigel's case, he even approached investors he knew and offered to buy the company himself.

  • When attempting a self-acquisition of the company, acting aggressively rather than iteratively is advisable until you form a suitable acquisition group.

  • A good CEO should consider what suits him in such a sales process. But, in any case, he should also act in a way that is right for the company.

  • Although the CEO is not a party to the sale/acquisition, he can become the most influential factor, with more power than the seller and the buyer. You can interview the parties instead of providing them with information, and you can act according to what you learn is essential to them to change the picture.

New Investors

  • When seeking an investor who will serve as a desirable future parent company, it is advisable to act with full force and leverage your entire network, your peers' network, and your acquaintances' network. Some may be relevant as an investor; others can provide sound advice or additional perspective, introduce you to another investor they know, and perhaps even want to invest after meeting you, despite not initially intending to do so (investors like to invest when they see the CEO).

    An excellent way to secure a meeting is to schedule it under the pretext of seeking good advice.

  • Understanding the right incentive can dramatically impact the deal. Understanding investors' strategies and goals can help you interact more effectively with them.

    When choosing an investor, it is fitting that the investor can execute the decision. This is even more important than the chemistry with the potential investor.

  • It is legitimate to stand your ground for the company's and employees' benefit and your benefit (including money). It is advisable to seize every such process as an opportunity.

    In negotiations, when you are not selfish, you often achieve outcomes that serve you best.

Decisions - Relationship with Managers

Replacing the Senior Management Team (Layoffs)

When a CEO is appointed to a job, they must ensure that the management team directly reporting to them is good enough and that they trust them.

If this is not the case, it is right to replace the team and bring in their trusted people - as quickly as possible.

Remember that every manager is loyal to the person who hired them. This is a double reason to replace the managers under you: the existing ones are loyal to someone else, and those you bring in will be loyal to you.

Recruiting a New Senior Management Team

After a CEO lays off part of the management team unsuitable for the company's new direction, they should strive to recruit a new team as soon as possible. This decision is not apparent, as it is not always clear that rapid recruitment will be error-free (and even more difficult in Seigal's case, where he wanted to prioritize women and workplace diversity). Nevertheless, the unequivocal recommendation is due to the many risks of leading a new path without supportive managers. Seigal [relied on the network of peers he had developed over the years and their recommendations to succeed.

Tips for hiring managers:

  1. Do not rely on referrals that a candidate brings. Need to be more reliable.

  2. Hire a management team whose skills complement the CEO's (not someone similar in their strengths).

  3. Multi-level interviews for the hired manager:

    1. The final decision maker guides on the role's 3-5 most critical abilities.

    2. The hiring team will decide which abilities will be examined by which interviewers.

    3. The decision maker will listen to the interviewers' opinions, mainly in the context of red flags, if any.

    4. The decision time must be bounded; such recruitments tend to drag on.

  4. Assist the newly hired person in succeeding in their role. Provide them with all possible information before or after entry so they can learn. Praise the hired person in front of the employees and peers already in the company.

  5. Investing in the cohesion of the management team, especially the veterans versus the newcomers.

Decisions - Working Relationships with Employees

Initial Trust Building

It is critical to build trust immediately.


  1. Initial, in-depth onboarding email.

  2. Reaching out and connecting with employees even before taking on the role via LinkedIn

  3. Kickoff meetings with groups of employees

Transparency with Employees and Direct Communication on Meaningful Challenges and Critical Changes Impacting Employees

Transparency with employees regarding significant challenges facing the company and critical changes it needs to implement as much as is reasonable and possible. When it comes to layoffs, it is advisable to be transparent regarding the challenges the company is facing (explaining the rationale for layoffs) while withholding information to a level that will prevent chaos—a one-time announcement to employees about the layoffs to prevent anxiety and rumor mills.

Support for employees and offers of assistance regarding jobs at other companies, while opening a door for them and providing recommendations.

Communication with Employees

  • After a wave of layoffs, preventing further departures is impossible. The people who left are in social, and perhaps even close, contact with those who remained in the company. It is advisable to demonstrate courtesy towards those who choose to leave. This contributes to the company since if they had remained unsatisfied, they would have culturally undermined the company and made things difficult. Increased effort should be invested in communicating with those who stay. The communication should be honest and open, yet strive not to succumb to promises that will be difficult to commit to (Siegel himself failed and promised there would be no more layoffs, which subsequently was not up to him and greatly hindered making optimal decisions for the company).

    Following the layoffs, one should be prepared for negative feedback and work to build trust in the company and, thus, in the employees.

  • Communicating major news should be simplified. The emphasis should be on its implications for employees (WIFM)

Deciding on Employee Headcount

  • Deciding on the proper employee headcount requires long-term thinking. If there is no choice, cuts should be made. Postponing (like a band-aid—painful but immediate) is wrong. Sometimes, you can accomplish more and move faster with fewer people.

  • Balancing engineers and salaried employees who constitute a core infrastructure versus outsourced employees from countries with lower employment costs to increase profits and enable growth.

Flexible Management

Employees are encouraged to make decisions on their own; when they do not prove themselves and trust in them is impaired, it is recommended that they forego empowerment and be managed tightly until it is proven that their judgment can indeed be relied upon. There are times when an excess of options makes things difficult for employees, and tight management helps them make the right decision.

Decisions - You! Relationship with Yourself

Deciding Whether to Take the Job Offered

This is the first decision every CEO (and other role holders) must make.


  1. Detach from the accompanying title and focus solely on the job itself.

  2. Ask yourself not only if it is the right job but also if it is the right one for you.


  1. Job interviews can be a tool for evaluating you and for selling you to the organization.

    It is advisable to find an opportunity to sell to the organization that you are connected to the purpose they are advancing. Every interview is a negotiation; everything is open to negotiation.

  2. After you are hired, they will remember what you promised. The interview creates expectations; this should be considered.

  3. If you left a job, conduct a lessons-learned exercise with yourself. So you do not return to the same type of challenge again.

Transferring Leadership (from a Previous Role Holder to You) Through a New Vision

Creating a new vision, almost immediately after taking on the role, that respects the past but offers how to upgrade it.

Critical as a tool for transferring leadership, especially when it is being transferred from a company's mythological founder to you.

Communicating the Leadership Philosophy

It is not possible to communicate everything. Even when it comes to complex and challenging decisions, when changing direction, the focus should be on communicating your leadership philosophy rather than on all the details of the derived decisions.


  • Supporting and pushing the team

  • Data-driven wins (analytics)

  • Integrity

  • Revenue

  • Transparency

  • Learning

  • Inclusive and diverse culture

  • Performance-driven culture

  • Focus

  • Emotional intelligence

Understanding Limitations

Despite their lofty position, a good CEO understands that they cannot influence everything. A good CEO needs to:

  1. Ensure a good management team under them.

  2. Define the strategic direction for the company's progress.

  3. Institutionalize strategic, financial, and managerial processes that guide decision-making in the company.

Conduct During a Significant Mistake "Disaster"

  1. In the event of a significant mistake, it is advisable to confront the truth—immediately acknowledge the failure, apologize, and move on. Removing yourself from the equation and ignoring personal feelings as much as possible is essential since the CEO's ego is not what matters currently. Also, the CEO is always under a microscope. That is part of the definition.

  2. Every failure is also a learning opportunity. It is not right to miss the learning.

Conduct During Significant Difficulties

  1. Even if there is turmoil and a dizzying rollercoaster, if a significant decision needs to be made, it is right to take a break (even half a day or a day) and think in a detached place.

  2. It is advisable to consult with others - there are many people out there who want and can help.

  3. When highly drained from the difficulties - one must be patient; often, the end of the difficult stage is near, and thinking about the next stage, and perhaps even the good involved in it, can be an encouraging factor to help get through the period.

  4. Relying on gut feelings is advisable when making decisions. If something seems wrong, it is never advisable to try and go that way.

Family and Home

No matter how busy you are, prioritize the home if there is a family need.

You - Outside the Office

Be yourself; relax.

Stick to the basic principles presented above - even in your personal life.

Don't give up. Don't underestimate your ability to influence your future. Always stay "in the game". Don't be afraid to fail.

Strong connections can make an impact. Indirect influence is also significant.

And may it be... good luck!

Appendix - List of Challenges for Which Decisions Need to be Made

0. Whether to take a specific job?

1. How quickly do you make changes upon entering a new position? (Appointing managers)

2. How to build trust among employees as quickly as possible?

3. How to successfully transfer leadership from a previous position holder to the new CEO?

4. How to save a company headed for a crash?

5. What is the right way to build an initial strategy for a company?

6. How to communicate a change of direction involving tough decisions?

7. How to deal with the parent company that owns the company you manage?

8. What should be done when a conflict exists between the company's interests and the parent company's?

9. Should you merge a company's organizational culture to match that of the parent company?

10. How to deal with a volatile manager/owner?

11. How much can you rely on the parent company saying it doesn't care about your losses?

12. How to set layoff targets (downsizing reorganization)?

13. How transparent should you be regarding layoffs?

14. How to prevent excessive staff departures after a significant wave of layoffs?

15. How quickly should you recruit a new management team?

16. How to interview a candidate for an executive position?

17. What type of strategy is suitable for the second year? Precise data-driven, which takes time to prepare, or partial but quicker?

18. How and when do you make the company honest (a company with a clear path to profitability)?

19. How to manage the company's culture?

20. Should you empower those you don't fully trust or manage them tightly?

21. How to implement a growth strategy?

22. What to do when there is a mass exodus of employees?

23. When should critical changes impacting the company (e.g., separation from parent company, major layoffs) be communicated?

24. How transparent to be with employees regarding the challenges facing the company?

25. What to do when the parent company decides to sell the company you head?

26. Should you dare to be the "bad guy" vis-a-vis the parent company at personal risk as CEO?

27. What is the best way to sell a company? Whether to approach potential buyers iteratively or blitz them?

28. What should the true motivation of the CEO be in an acquisition/sale process? What's best for him or what's best for the company?

29. In the event of a significant mishap ("disaster"), is it right to bury it or confront it?

30. How to find an investor for the company?

31. How to deal with failure?

32. Is it advisable to realign all goals if you know everything is lost?

33. When you are not the decision maker but only an influencer, how can you have more power than the decision makers?

34. What to do when the CEO's and owners’ goals are not aligned?

35. What to do when there are no good options?

36. What to do when you are against the wall because all options are bad?

37. How to conserve energy during periods of extreme exhaustion?

38. When is it right to rely on gut feelings?

39. How to communicate big news?

40. When is it right to make a significant change of direction for the company you manage?

41. How to assess whether the change of direction chosen is successful and the right decision?

42. How to plan for an unknown future?

43. How to create a strategic plan that is inspiring yet achievable, focused, flexible, realistic, and ambitious at the same time?

44. How to apply what you've learned in your career to your personal life as well?

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