As an experienced CMO (Chief Marketing Officer) and entrepreneur in the dynamic realm of startups, I’ve learned the art of speaking truth to power and steering CEOs toward better decision-making. The journey is fraught with challenges, as delivering unpalatable truths and guiding leaders away from their impulses requires tact, strategy, and a deep understanding of human psychology. Here’s how I’ve navigated these waters without (most of the time hehe) inciting conflict or controversy.

Understanding the CEO’s Perspective

Firstly, understand that CEOs are under immense pressure to make decisions that impact the entire company. Their resistance to bad news or divergent opinions often stems from a mix of stress, responsibility, and attachment to their vision. Empathize with their position but recognize that part of your role is to be the voice of reason and long-term strategic thinking.

Establishing Trust

Trust is the cornerstone of any relationship, particularly in a startup environment where stakes are high and resources are scarce. Build trust with your CEO by consistently delivering results and demonstrating your expertise. When trust is established, your words carry more weight, and the CEO is more likely to consider your perspective, even if it’s contrary to their initial instincts.

Communicating the Hard Truths

Delivering hard truths to a CEO demands a balance between straightforwardness and tact. Use clear, concise language to minimize misunderstandings, while maintaining respect and empathy. Back your points with data and evidence, as factual arguments tend to resonate more effectively. It’s vital not only to highlight problems but also to propose viable solutions or alternatives. This approach showcases your commitment to the company’s success and establishes you as a strategic asset, adept at handling complex challenges with insight and tactfulness.

When delivering difficult news or a differing opinion:

  • Be Direct but Tactful: Use clear, concise language. Avoid jargon or ambiguity. But ensure your tone is respectful and you acknowledge the CEO’s perspective.
  • Focus on Data: Support your arguments with data and evidence. CEOs are more likely to listen to logical, data-driven arguments than emotional pleas.
  • Offer Solutions, Not Just Problems: When highlighting a problem, also present potential solutions or strategies to address it. This shows that you’re not just a critic but a problem-solver.

Steering Away from Poor Decisions

Averting poor decisions by the CEO isn’t always possible, but when it is, it involves a strategic approach. Understand their motivations to align your counterarguments with their goals, emphasizing the risks involved. Present safer, strategic alternatives, and use industry precedents and historical data to underscore your points. This not only helps in immediate situations but also fosters a culture of informed, data-driven decision-making in the startup.

If you believe the CEO is about to make a detrimental decision:

  • Understand their Motivation: Try to understand why they are leaning towards a particular decision. Address those motivations in your counter-argument.
  • Present Alternatives: Offer alternative solutions that align with their ultimate goals but mitigate potential risks or downsides.
  • Use Precedents: Highlight examples from the industry or the company’s past where similar decisions led to negative outcomes, or conversely, where different decisions led to success.

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Encouraging Autonomy

To foster autonomy, it’s crucial to remind the CEO of your past successes and the expertise that led to your hiring. This reinforces the trust in your decision-making skills. Clearly delineate roles and responsibilities, openly discussing the need for independence in your function while ensuring the CEO remains informed and involved. Proposing a trial period for your strategies with defined success metrics can be an effective way to demonstrate the efficacy of your approach, easing any concerns the CEO might have. This method not only asserts your autonomy but also builds a cooperative environment where both parties feel valued and heard.

If you find the CEO micromanaging or doubting your decisions:

  • Remind of Past Successes: Gently remind them of instances where your strategies paid off. Reinforce the idea that they hired you for your expertise and track record.
  • Set Clear Boundaries and Expectations: Have an honest conversation about roles and responsibilities. Express your need for autonomy in decision-making, while also outlining how you’ll keep them informed and involved.
  • Propose a Trial Period: If they’re hesitant, propose a trial period for your strategy with predefined success metrics. This shows confidence in your plan and provides a structured way to prove its efficacy.

Maintaining a Positive Dynamic

Preserving a positive dynamic with the CEO is pivotal for a CMO in a startup. This involves consistently exhibiting professionalism and respect, especially during disagreements. Embrace feedback and remain receptive to constructive criticism, demonstrating your commitment to collaboration and growth. Regular communication is key; don’t limit interactions to formal meetings. Frequent, informal updates can prevent misunderstandings and strengthen your rapport. This approach not only helps in building a robust working relationship but also ensures a harmonious and productive atmosphere conducive to the company’s success.

Throughout all interactions:

  • Stay Professional and Respectful: Even in disagreements, maintain a professional demeanor. Respect goes a long way in preserving a healthy working relationship.
  • Seek Feedback and Be Open to Criticism: Show that you value the CEO’s input by actively seeking their feedback and being open to criticism. This fosters a collaborative, rather than confrontational, dynamic.
  • Communicate Regularly: Don’t wait for formal meetings to update or consult with the CEO. Regular, informal check-ins can prevent misunderstandings and build a rapport.


Navigating the delicate dance of managing upwards as a CMO in a startup involves a blend of empathy, strategic communication, and assertiveness. By building trust, articulating truths with tact, guiding decision-making through data and alternatives, and fostering a positive dynamic, you can influence your CEO effectively while avoiding conflict. Remember, your ultimate goal is to guide the company towards success, and sometimes that requires steering the ship with a gentle but firm hand. With these strategies, you can enhance your relationship with the CEO, contribute to your company’s strategic direction, and reinforce your value as a pivotal member of the leadership team.

About the Author: Jeremy Mays

Is the Founder and CEO of Transmyt Marketing. He's an accomplished, award winning marketer, responsible for guiding companies though the complex challenges of navigating and succeeding in today's digital economy. To get in touch, you can email him at

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