Why not asking for what you want is holding you back | Kenneth Berger (exec coach, first PM @Slack)

Kenneth’s background (00:00:00)

• Kenneth Berger is a former product manager at Slack and an executive coach.
• He transitioned into coaching to help startup leaders avoid burnout and achieve their goals.
• His core focus is teaching leaders how to ask for what they want.
• People pleasers tend to hope that others will read their minds and fulfill their needs.
• Control freaks tend to order people around and expect immediate compliance.
• Complaints can be a source of inspiration for envisioning a better future.
• Asking for what you want increases the chances of getting it.
• To figure out what you want, pay attention to your complaints and envision a better future.
• Asking for what you want effectively involves:
  • Overcoming resistance.
  • Communicating your desires clearly.
  • Listening to the response you receive.
• Listening to the response to your request is crucial.
• The response can provide valuable information and insights.
• It allows for adjustments and further discussions to reach a mutually beneficial outcome.
• Improved communication and relationships.
• Increased confidence and self-esteem.
• Greater satisfaction and fulfillment in personal and professional life.
• Ability to achieve goals and aspirations more effectively.

The importance of asking for what you want (00:04:31)

• Asking for what you want is crucial for integrity and personal fulfillment.
• Many people deceive themselves about genuinely pursuing what they want in life.
• Not asking for what you want leads to stress, frustration, and unhappiness.

Challenges that arise when people struggle to ask for what they want (00:06:36)

• People get stuck in the same frustrating situations due to not asking for what they want or not learning from their experiences.
• Interpersonal conflict can arise from holding back or coming across as entitled when asking for what you want.

A personal example of failing to ask for what you want (00:08:09)

• Kenneth Berger shares a personal example of how his attachment to being right hindered his ability to ask for what he wanted.
• He emphasizes the importance of being open to other ideas and perspectives, rather than assuming that one is always right.
• Berger stresses that going into a meeting with a sense of righteousness can be disrespectful and hinder productive conversations.

Signs this is a skill you need to work on (00:09:17)

• Indicators that you need to work on asking for what you want include feeling stuck in your career or experiencing frequent interpersonal conflicts.
• High-stakes situations can exacerbate the difficulty of asking for what you want, as the fear of negative outcomes can overshadow the desire for positive outcomes.
• When the stakes feel high, people tend to focus more on avoiding what they don't want rather than achieving what they do want.

How to get better at knowing what you want (00:10:49)

• Knowing what you want and asking for it is essential for personal fulfillment.
• The "dream behind the complaint" technique helps uncover underlying desires by examining complaints.
• Complaining implies a better world where the complaint is resolved, revealing a vision of what one truly wants.
• Articulating what you want is the first step in the process of asking for it.
• The resistance to asking for what you want often stems from the fear of failure, rejection, or not getting it.
• The process of asking for what you want involves articulating your dream, asking for it, and accepting the response, whether positive or negative.

Why hearing “no” is a normal part of the process (00:15:28)

• Redefine "no" as anything short of an enthusiastic "hell yes".
• Accept "no" as valuable data to help you refine your approach.
• Don't settle for a "maybe" or "I'll try"; ask for what you truly want.
• Reframe the conversation to find a mutually agreeable solution.

Getting a “yes” vs. a “hell yes” (00:17:29)

• A "hell yes" is when someone fully agrees and is enthusiastic about something.
• A "yes" without enthusiasm often leads to lack of follow-through.
• Pay attention to your body's cues to recognize a genuine "hell yes".
• This concept applies to all areas of life, not just startups.
• In the startup world, you must be comfortable with uncertainty and failure.
• Embrace the perspective of pursuing meaningful goals even without guaranteed success.
• Detach from the expectation of getting what you want and focus on the value of pursuing it.

Step 1: Articulate what you want (00:19:20)

• Clearly articulate your wants without being overly attached to the outcome.
• Focus on realistic social-emotional goals rather than unrealistic expectations.
• Provide specific feedback and consequences when necessary, even if it's difficult.
• Strive for alignment, but be prepared to "disagree and commit" when necessary.
• Don't be afraid to ask for what you want, even if it means upsetting others.
• It's important to come to terms with what you truly want to do, even if it means upsetting people.

Doing an integrity check (00:24:07)

• Paying attention to what would make things better or run more efficiently is a way to identify what you want.
• An integrity check involves fully expressing yourself, including acknowledging and expressing your feelings.
• Articulating what you want requires mindfulness and checking for unexpressed parts of yourself.
• Expressing what you want can alleviate suffering and fear that arise from holding it in.
• Integrity is key to figuring out what you want.
• Look for opportunities to fully express yourself.
• Pay attention to recurring thoughts or desires that you haven't addressed.
• Expressing what you want is about mindfulness and self-awareness.

Step 2: Ask for what you want intentionally (00:26:56)

• Asking for what you want intentionally involves recognizing the rut you get stuck in and working through the narratives that make you resist asking differently.
• People who don't want to ask often have stories that say it's too risky or not worth it.
• Not asking for what you want has a serious cost, as you end up not expressing who you are and what you stand for in the world.
• It's important to bring compassion for yourself when asking for what you want, as there's no guarantee that people won't be mad or that you'll get your dreams come true.
• Not pursuing your dreams because of the fear of upsetting others is not worth it.

Understanding your influence (00:30:45)

• People often underestimate their influence and power.
• Your relationships and opinions matter, even without data to support them.
• Being humble and vulnerable when asking for what you want can be effective.
• Leaning on data as a crutch can prevent you from speaking up.
• Gut opinions and subject matter expertise are valuable, even without hard data.
• Balancing asking clearly with great humility is important.
• Expressing disagreement and preferences while acknowledging others' perspectives can be effective.
• People care about your opinion and you can influence change by sharing it.
• Relying solely on data can overlook the value of relationships and personal beliefs.
• Being vulnerable and putting your thoughts out there, even without concrete evidence, can be powerful.

Using complaints as inspiration (00:34:48)

• Complaints can be a sign that you should be asking for what you want.
• Complaints can be great inspiration for envisioning a better future and finding an effective way to communicate your desires.
• Embrace the frustration and complaining, and follow that thread down to find an effective way to move towards your goals.
• Embrace the "whiny" part of yourself and take what it has to say as important data.

Internal family systems (00:36:24)

• Internal family systems is a psychotherapy technique that talks about the different parts of ourselves and how they don't always agree with each other.
• Embracing and validating all of our parts is important for asking effectively.
• If we ignore the part that's scared to ask, we'll stay stuck.
• By embracing our fears and acknowledging them, we can soften them and move past them.

Giving feedback (00:38:00)

• Carol Robin, who taught a class at Stanford on interpersonal skills, shared a framework for giving feedback that people can receive.
• The template for giving feedback is:
  • When you do [behavior], I feel [feeling].
  • Be specific about the feeling, not just "I feel like" or "I feel that."
  • State the reason for giving the feedback, and what you want the person to change.
• This approach is similar to Nonviolent Communication and Dialectical Behavioral Therapy (DBT), which emphasize staying factual and focusing on thoughts, feelings, and observations.
• Avoid getting distracted by stories or interpretations of the data.
• Be clear and specific about what you want.

Step 3: Accept the response (00:41:24)

• Accepting the response is challenging because people tend to be biased towards hearing a "yes" and may over or under-accept a "no".
• Over-accepting a "no" means believing it is permanent and never asking again.
• Under-accepting a "no" means disregarding it and disrespecting the other person's ability to consent.
• Genuine respect for the other person's decision can actually be more influential and motivating than trying to force or coerce them.
• Preparing for rejection and understanding that "no" is a common response is important.
• Acceptance of the response is primarily an emotional regulation issue, as it involves managing the negative feelings that come with hearing "no".
• Getting good at asking for what you want requires recognizing that hearing "no" is normal and learning from it to try different approaches in the future.

Kenneth’s experience of being fired three times from Slack (00:45:22)

• Kenneth Berger, a former PM at Slack, was fired and rehired three times due to misalignment of expectations and lack of communication.
• Initially overconfident, he failed to clarify his goals and the company culture, leading to misunderstandings and his first termination.
• Despite being rehired, he became a people pleaser, fearing consequences and negatively impacting his job satisfaction and relationship with the CEO.
• Not expressing desires can result in negative outcomes, while articulating them increases the chances of fulfillment.
• Inability to handle rejections and criticisms can lead to self-deception and blaming others, emphasizing the importance of emotional regulation in accepting and learning from negative feedback.
• Staying true to oneself, even in difficult situations, is crucial for personal and professional growth.
• Asking for what you want, listening to feedback, and maintaining authenticity can help turn around challenging circumstances.
• Articulating desires and intentionally creating outcomes are essential for success, even if the desired outcome is not guaranteed.
• The practice of asking for what you want is not just about achieving specific goals, but also about maintaining integrity and avoiding suffering.

Advice on being the first PM at a company or startup (00:57:30)

• Establishing a positive working relationship with the CEO or founders is essential for success as the first PM at a startup.
• Have an open and honest conversation with the founders when you're first hired to clarify expectations and roles.
• Don't hesitate to express your needs and wants, as many founders may appreciate your honesty.
• Overcome the fear of not being good enough by recognizing that fear is not always functional and that focusing on a vision and goals is more effective.
• Find intrinsic motivation and align actions with one's desires for sustainable goal achievement rather than relying solely on discipline.

Contrarian corner: anti-discipline (01:04:58)

• The speaker does not believe in strict discipline as a long-term solution for motivation.
• Shouting or being strict may work for a short time but not for years.
• True long-term motivation comes from relying on vision and pursuing what you want.
• Knowing what you want, asking for it, and dealing with the answers you get are key to achieving your goals.

Lightning round (01:05:52)

• Kenneth Berger, a former product manager at Slack and current executive coach, recommends several resources for personal and professional development:
  • "Radical Candor" by Kim Scott and "The 15 Commitments of Conscious Leadership" for personal growth.
  • Johnny Miller's "Nervous System Mastery" course for understanding how to work through resistance.
  • The Netflix documentary "Breakpoint" for insights into the mental side of tennis and overcoming self-limiting beliefs.
  • The movie "Living" for its exploration of finding purpose and fulfillment in life.
• Berger also emphasizes the importance of asking for what you want and encourages individuals to be more assertive in pursuing their goals.
• He recommends joining his LinkedIn community and subscribing to his newsletter for further discussions and ideas on this topic.
• Berger is currently writing a book about asking for what you want and values community feedback to enhance its effectiveness.