John Gauch John Gauch

Why Startup Founders Need Thinker-Doers for Their Teams

Startup founders need thinker-doers—individuals who can balance analysis, idea generation and implementation. These are the talented people who thrive in fast-paced, resource-limited environments. Hiring and nurturing thinker-doers will accelerate your progress and improve the odds of your startup succeeding.

Graphic featuring the thinker-doer term with imagery representing thinking and doing

Image created using DALL-E by OpenAI.

By way of introduction - I'm a hands-on, seasoned fractional COO (Feldspar, FreshAhead, Synervoz), sales coach (Microsoft), and mentor (Alumni Ventures, High Alpha). Over 20+ years, I have applied my growth and operations skills to help dozens of startups (IAN, Axiom, Spartan). I'm excited to share my ideas and thoughts here. I hope you find them useful on your startup path.


Introduction

Fellow IBMer Fred Brooks, a leader in software engineering and computer science, once said, "Thinkers are rare; doers are rarer; and thinker-doers are rarest." This idea isn't just relevant to building leading tech—it's useful for anyone trying to build an agile, proactive, fast-moving team, especially startup founders.

Key Takeaways

  1. Thinker-doers balance strategy and execution.

  2. Thinkers and doers have value, but over-reliance on either will create issues, especially at startups.

  3. Hire thinker-doers by seeking real-world examples of execution.

  4. Lead thinker-doers with clear goals and consistent feedback by providing them with plenty of autonomy.

Why Thinker-Doers Are Essential in Startups

Brooks introduced the concept of thinker-doers—individuals who can strategize and execute their strategies—in The Mythical Man-Month. Thinker-doers thrive in environments where they can analyze and assess information, design solutions and implement their ideas. This makes them not just valuable, but essential to the success of startups.

In startup world, resources are limited, and frequent decision-making and follow-up are required. Thinker-doers can develop ideas and bring them to life without relying on someone else to execute them. This self-sufficiency avoids failed handoffs and speeds up activity while tightly aligning vision with execution.

Startups that lean too heavily on either thinkers or doers face inevitable roadblocks. Thinkers can get lost in analysis or ideation, slowing progress without clear action steps. On the other hand, doers may focus solely on completing tasks, sometimes missing the bigger picture or long-term goals. Balancing these tendencies is where thinker-doers shine; they combine both mindsets to keep a startup moving forward with the practical application of a vision.

Overweighting the team with thinker-doers is particularly critical for post-Seed to Series A startups and bootstrapped firms looking to tap into the same growth curve as those startups. Too many thinkers will stall execution, while too many doers may result in committing too many resources to the wrong paths forward. Getting this right requires careful people recruitment and management.

The Role of Pure Thinkers or Doers

While thinker-doers are the ideal startup profile, thinkers and doers can still play roles in specific situations. Thinkers often excel in advisory roles, offering strategic input without taking responsibility for execution. They can be especially valuable as external advisors or mentors, for example. However, you need to test whether thinkers have past experience executing their ideas. Be wary of contributions from thinkers who share theories or pass on recommendations based on others' lived experiences or lacking any history at all. Evaluate all of their suggestions carefully and cautiously. Many people are happy to offer opinions, so I'd be concerned about having too many "idea" people kicking around, offering too many perhaps conflicting recommendations.

Read also: Defining our Terms: What is a Fractional Leader Anyway?

Doers' potential contributions are more limited at startups. Even for a simple or repetitive task, mindful execution matters. There aren’t going to be many, if any, workstreams or processes that work perfectly at a startup. If they operate smoothly, they will still be subject to change as the business evolves. For even the most routine work, I'd prefer doers who consider how their work contributes to the company's customer-driven purposes. So, they are doers who bring a reflective and thoughtful approach to their work.

Be on the lookout for this one doer, gotcha, from the person who comes up with a single option to a problem or opportunity and acts on it immediately without surfacing alternatives. Maybe they get lucky, but more often, we’ll find out it wasn't a great idea at all. Lack of reflection and option-building by doers can waste a lot of time, which is always in short supply for startups.

If you find that you've employed or engaged a thinker or a doer, determine as quickly as possible if this is an ingrained trait or a behavior subject to quick change. All human beings are capable of personal development and growth. But for some people, this can happen at a glacial rate. You don't have that kind of time. Suppose a challenging teammate can't adapt quickly. In that case, move that person toward the exit sooner rather than later. That's the most respectful way to handle the situation for all parties.

Read also: Overlooked Traits of Successful Startup CEOs

How to Spot a Thinker-Doer When Hiring

Identifying thinker-doers during the hiring process can be hard, but there are practical ways to spot them. Start by asking candidates to share specific examples of when they took an idea from conception through execution. Look for clear instances of both creative thinking and follow-through.

During interviews, present scenarios where a candidate must balance strategy and action. For example, ask them how they would handle a sudden pivot in company direction or how they'd prioritize competing goals in a resource-constrained environment. Do they gravitate toward doing a ton of analysis and hours of desk research? Or do they emphasize learning by doing? Look for a bias to action in their replies.

I'm not advocating for “firing” without “aiming,” by the way. I am promoting people developing informed hypotheses and testing them out in real-life experiments to get answers quickly that aren't mere guesswork.

Finally, ask for stories demonstrating real-world problem-solving and follow-up. In the case studies they share and prior work experience they describe, consider whether they naturally cover both angles. A candidate leaning heavily toward thinking or doing may struggle with speaking to the other aspect convincingly. A candidate's past success in managing uncertainty by identifying options and taking action steps to discover the best path will contribute mightily in a startup environment.

Read also: More Overlooked Traits of Successful Startup CEOs

How to Lead and Support Thinker-Doers

Once you've hired thinker-doers, be sure to support them. Regarding people's performance, I keep in mind an acronym from Dan Pink: AMP-R. I added the "R."

  • "M" stands for mastery.

  • "P" stands for purpose.

  • "R" stands for relationship.

  • "A" stands for autonomy.

Thinker-doers thrive when given autonomy, and they'll reach peak performance when this is combined with the other acronym qualities, all in alignment with company goals. They will flourish if you allow these teammates to be creative and proactive when you have set clear expectations for outcomes. Do not micromanage a thinker-doer. That is certain to backfire.

Thinker-doers appreciate ownership of their work and will benefit from timely feedback that helps them improve. You might also establish a regular check-in, emphasizing your teammate’s personal development and broader career goals. Coach and help them to reach high levels of performance. Don’t take autonomy to an extreme. Accountability is critical; thinker-doers perform best when trusted and held responsible for the outcomes they drive.

Read also: 50 Top Apps, SaaS Solutions, Services, and Sites for Startups


Spartan vs Tough Mudder

It is interesting to see how organizational cultures end up reflecting the styles of their team members. During my time at sports indusry innovator Spartan, the CEO, Joe DeSena, was known for his fast-paced, action-oriented style. He leaned heavily on a "fire-aim-ready" mentality, leading to rapid iteration and learning. In contrast, arch-rival Tough Mudder had a slow, deliberate approach—focusing on analysis and planning over doing.

While Tough Mudder’s impressive cohort of business school graduates and former management consultants developed top-notch PowerPoint decks, they were slow to test ideas in the real world, limiting their pace of learning. They didn't develop conviction around a path forward. They lacked a competitive strategy supporting a clear customer-driven purpose. In the end, Spartan acquired Tough Mudder, achieving Spartan’s objective of becoming the Iron Man of obstacle racing.


Conclusion

The “first product" of a startup must be the team. If a team implodes (which definitely happens), it's game over. Creating a startup team of thinker-doers will improve your odds of startup success. While thinker-doers are ideal for most situations, thinkers may bring value when used strategically and sparingly. Over-indexing on pure thinkers or doers or relying on smooth handoffs between the two types of people will be a costly approach.

Building a successful early-stage startup is about turning unknowns into knowns by taking action—mindfully and methodically testing ideas and learning from those actions. Thinker-doers are your best bet for developing great ideas and putting them into action.

By hiring and nurturing thinker-doers, founders can shorten the time it takes to find product-market fit and then scale up. Fostering an environment that encourages creativity, action, and accountability will help every one of these team members reach their fullest potential. Your smartly staffed, well-coached team will keep your startup in action, focused on its long-term vision, while staying agile to handle daily challenges.

I love to connect with other like-minded startup leaders. Read more about me here, and please reach out.

I wrote this blog post with the help of a personalized GPT from OpenAI that I customize and train.
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John Gauch John Gauch

Essential Leadership Skills for 2024: What They Are and Why Every Leader Needs Them

Building a successful startup is one of the hardest challenges you can take on. Read about and develop essential leadership skills for 2024 and beyond, including self-awareness, strategic thinking, and adaptability, to improve your odds of succeeding.

Listen to the podcast version of this blog post, an AI experiment.

Graphic illustration of leadership showing someone leading a group of people up the bars of a bar chart

In case you’re new here - I'm John Gauch – a seasoned fractional COO, sales coach and mentor. Over 20+ years, I have applied my growth and operations skills to help dozens of startups, building one high-impact venture to nearly $100M in revenue and a second to exceed that benchmark. I began my career as a tech lawyer in New York City and developed my expertise in progressive roles in business development, finance, sales, marketing and product, working along the way with companies like Amazon, IBM and Microsoft.


As we navigate the complexities of today’s volatile and uncertain economic environment, the role of a leader has never been more critical. In an era defined by rapid technological advancements, global interconnectedness, and unprecedented challenges, the skills that made leaders successful in the past are evolving. Let’s explore the essential leadership skills you need to thrive in this dynamic environment. Whether you're looking to enhance or develop new abilities, this guide will provide you with the insights necessary to lead effectively in 2024 and beyond.

The Core Leadership Skills for 2024

Self-Awareness

Self-awareness is the cornerstone of effective leadership. In 2024, leaders must deeply understand their strengths, weaknesses, emotions, and motivations. This awareness allows for authentic leadership, fostering trust and respect among team members. Regularly reflecting on your actions and seeking feedback can enhance your self-awareness. Developing this skill not only improves your decision-making abilities but also helps you build stronger relationships with your team, leading to a more cohesive and productive work environment.

Vision and Strategic Thinking

Having a clear vision and strategic thinking is essential in an ever-changing business landscape. Visionary leaders inspire their teams by articulating a compelling future and setting strategic goals to achieve it. This skill involves anticipating market trends, understanding competitive dynamics, and aligning your organization's resources accordingly. Strategic thinking requires a balance of analytical skills and creativity, enabling you to navigate complexities and seize opportunities. By cultivating a strong vision and strategic mindset, you can steer your organization towards long-term success.

Communication

Effective communication is a fundamental leadership skill that applies to all aspects of management. As a leader in 2024, you must be adept at conveying your ideas clearly and persuasively, whether in person, through digital channels, or in writing. Active listening is equally important, as it helps you understand the perspectives and concerns of your team. By fostering open and transparent communication, you can build a culture of trust and collaboration. Strong communication skills also enable you to resolve conflicts, motivate your team, and drive organizational change.

Read also: Overlooked Traits of Successful Startup CEOs

Adaptability and Agility

In today's fast-paced world, adaptability and agility are critical for leadership success. Leaders must be able to pivot quickly in response to changing circumstances, whether it's a market shift, technological advancement, or internal organizational change. This skill involves being open to new ideas, embracing uncertainty, and continuously learning. By fostering a culture of agility, you can ensure your organization remains resilient and competitive. Adaptable leaders are not only better equipped to handle challenges but will also capitalize on emerging opportunities.

Empathy and Compassion

People of all kinds have increasingly recognized empathy and compassion as vital leadership traits. In 2024, leaders must prioritize understanding and addressing the needs and emotions of their team members. Empathetic leaders build stronger connections and foster a supportive work environment, leading to higher employee satisfaction and retention. Compassionate leadership involves showing genuine concern for your team's well-being and providing support during difficult times. Integrating empathy and compassion into your leadership style can create a more inclusive and motivated workforce.

Integrity and Ethics

Integrity and ethics are the bedrock of leadership. Leaders must uphold the highest ethical standards in an era where corporate transparency and social responsibility are paramount. This means being honest, fair, and consistent in actions and decisions. Ethical leaders inspire trust and loyalty, both within their organization and with external stakeholders. By prioritizing integrity, you can build a strong reputation and create a positive organizational culture that promotes ethical behavior at all levels.

Collaboration and Team Building

Effective collaboration and team building are essential for achieving organizational goals. Leaders in 2024 must be skilled at fostering a collaborative environment where diverse perspectives are valued, and teamwork is encouraged. This involves creating opportunities for team members to work together, facilitating open communication, and resolving conflicts constructively. Strong team-building skills help you harness the collective strengths of your team, leading to increased innovation, efficiency, and higher overall performance.

Innovation and Creativity

Innovation and creativity are critical drivers of business success in today's competitive landscape. Leaders must cultivate a climate where new ideas are encouraged and experimentation is valued. This involves challenging the status quo, supporting creative thinking, and providing the resources needed for innovation to flourish. By fostering a culture of innovation, you can drive continuous improvement and stay ahead of industry trends. Creative leadership will enhance your organization's adaptability and inspire your team to think boldly and achieve extraordinary results.

Read also: How to Become a Thought Leader in Your Industry

Why These Skills are Crucial

Understanding the importance of these leadership skills is essential for several reasons. First, they directly impact your effectiveness as a leader. Self-aware leaders, for example, can more accurately assess situations and make better decisions. Vision and strategic thinking ensure that your organization stays on the right path, even amid uncertainties. Effective communication fosters a transparent and collaborative work environment, crucial for maintaining team morale and productivity.

Statistics and studies underscore the importance of these skills (research on empathy, for instance). Certainly, organizations that prioritize innovation will see higher growth rates. By developing and honing these skills, leaders can drive their organizations toward greater success and stability. The ability to adapt quickly to changing circumstances is not just a competitive advantage but a necessity in today's fast-paced world.

Do some leaders achieve economic success without doing this? Do you have to build a company that’s a fantastic place to work to reach a big exit or secure another financial reward? Candidly, you do not, but why wouldn’t any thoughtful human being want to, especially if it might improve the challenging odds of building a successful startup?

Developing Leadership Skills

Developing these essential leadership skills requires a proactive approach. Start with self-assessment tools and definitely seek feedback from peers and mentors to identify areas for improvement. Consider enrolling in leadership development programs or workshops that focus on building specific skills such as strategic thinking, communication, and adaptability. Consider working with a development-focused executive coach. Make a point to include practical exercises and real-world scenarios in your learning experiences. Continuous learning is key.

Read books, attend seminars, and stay updated with the latest research. Be humble. Engage with a community of leaders through networking events or online forums to exchange ideas and experiences. Many private groups serve founders, and Operators Guild is a phenomenal group for top startup operators.

Remember, leadership development is a process. By committing to continuous improvement, you can ensure that you’re becoming a more effective and inspiring leader, capable of guiding your team through the challenges and opportunities of 2024 … and beyond.

Read also: More Overlooked Traits of Successful Startup CEOs

The demands on leaders are evolving. Embracing self-awareness, vision, communication, adaptability, empathy, integrity, collaboration, and innovation will make you a more effective leader and improve the odds of your organization reaching new heights.

Developing as a leader is a journey, and continuous learning is key. Nobody needs to do this alone, nor can you. If you’re a startup CEO, founder or entrepreneur, and you want to chat about your leadership goals and whether I can be helpful in some way, I’d love to connect. Please reach out.

A blogging experiment, this post was written with some help from AI.
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John Gauch John Gauch

More Overlooked Traits of Successful Startup CEOs

Last month, I highlighted six under-recognized traits of successful startup CEOs (entrepreneurs, founders) and detailed three in my blog. This week, I cover the next three, including what I mean when I say, “Focus on discovering what is right versus being right--quickly.”

Listen to the podcast version of this blog post, an AI experiment.

Successful and unconventional entrepreneur

Photo by Karolina Kaboompics from Pexels.

New here? I’m John Gauch – a seasoned fractional COO, sales coach and mentor. Over 20+ years, I have applied my growth and operations skills to help dozens of startups, building one high-impact venture to nearly $100M in revenue and a second to exceed that benchmark. I began my career as a tech lawyer in New York City. I developed my expertise in progressive roles in business development, finance, sales, marketing and product, working along the way with companies like Amazon, IBM and Microsoft.


This two-part post is about about critical, often-overlooked traits of startup CEOs (also, entrepreneurs, founders).

In the first post, I wrote how possessing the first three characteristics below is important but not enough to improve your odds of building a successful business.

  1. Creativity and vision.

  2. Passion for the product.

  3. Leadership skills.

  4. Perseverance.

  5. Risk-taking.

  6. Speed.

The following three traits—perseverance, risk-taking and speed—are also commonly associated with startup leaders. Reasonably so, but you must reconsider and expand your understanding of these ideas to be at your entrepreneurial best.

Sometimes, hard work doesn’t get you anywhere.

Challenges and hardships on the entrepreneurial path are inevitable. You do need to be strong and stick with it. Building a startup is an exercise full of uncertainty.

During the Build phase of a startup, there are many unknowns before you achieve product-market fit and solidify your business model. You have a hunch about what might work, but you don’t know with certainty how to reach the desired outcome. You may have it right, sort of right, or completely wrong. Blind dedication to an early hypothesis may get you nowhere.

Rather, you must be resolute and simultaneously open to the possibility that the path forward differs from what you think. Successful startup teams are experts at making unknowns known and reducing uncertainty. In the fastest learning loops possible, figure out what you need to know to solidify your business model. Focus on discovering what is right versus being right—quickly.

Get comfortable with uncertainty over taking huge risks.

You need to be comfortable with some risk if you are building a venture-backed startup or bootstrapped business with similar ambitions. You are taking on a mission into the unknown with many uncertainties after all. So you need to be okay with all that.

But successful entrepreneurship isn’t about gambling or making a single guess, chancing you have it right, and it will all work out.

Entrepreneurs must have a temperament that tolerates uncertainty and a drive to minimize risk—not take risks. Minimize risk by becoming a learning expert. Figure out what isn’t working, what might work, and test it out.

Another way to reduce risk is to carefully steward your resources by raising the capital you need, acquiring early customers and managing how you spend what you bring in. Give yourself and the team as many at-bats (i.e., as much time to learn) as possible.

Make time for what doesn’t seem necessary.

When you ignore or shortchange (or are bad at) the people side of your business, you’ll reduce the odds of your startup succeeding. If the team breaks down, all could be lost. If you succeed, you’ll either create a place where people hate to work or need to spend a lot of time and money later to fix a mess.

Instead, consider the organization a top priority or even your “first product.”

Culture results naturally from what we prioritize and how we do what we do every day. Build the organization daily by simply behaving the way you want the team to act. Be today the way you want the business to be tomorrow.

Remember the four Cs to start if you’re unsure how to do this. (I added one final C to Edgar Schien’s original three). Be curious, caring and committed when interacting with others, and be competent in your work. You’ll create a trusting environment where people want to work that will become self-sustaining.

Read part 1: Overlooked Traits of Successful Startup CEOs.

If you’re curious at all about me or what I do, see how I help startup CEOs, founders and entrepreneurs on my services page.

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John Gauch John Gauch

50 Top Apps, SaaS Solutions, Services and Sites for Startups

Startup CEOs and founders are very demanding when it comes to the tech they use to run their businesses. They have high expectations. They should, too. See how this list of apps, SaaS solutions, services, and sites lines up with your tech stack and hopefully get some new ideas for what to add or switch. Updated November 20, 2024.

Image for blog post about list of top tech for startups

Photo by Magda Ehlers from Pexels.

I hope you find this list helpful - I'm John Gauch, a consultant with extensive experience in business operations and growth. I specialize in helping startups implement both strategies effectively. As a fractional COO, I work with founders and CEOs through each step, tailoring solutions to your unique needs and objectives.


Updated November 20, 2024.

What started as a list of 50 startup products has grown well past that figure, and I’d love to keep adding to it.

I personally don’t find those lists or infographics of every possible product option for a problem I have super useful. I don’t need another time-sucking To Do, to evaluate all of the choices. I want to know what’s a reasonably safe bet, get started with it and turn back to the business of growing my company.

This list is biased toward Seed to Series A companies because that’s where I spend most of my time, although it also includes some products for brand-new companies (drawn from the venture studio work I do). With regard to each product on the list, I've either used it, and I recommend it, or someone I know and trust has used it, and they recommended it to me. That said, feedback is invited—if you feel like something should be added, or if you have used one of the products and had a negative experience. Email me and let me know.

If you ever need referrals to startup attorneys, message me to chat. As a former lawyer and former General Manager at legal startup Axiom, I know tons of incredible lawyers across specialties and fields, including top-notch solo practitioners as well as members of AmLaw 100 firms like Morrison & Foerster and Perkins Coie, regional players and startup boutiques.

I don’t mention project management tools (e.g., Asana, ClickUp, Monday, Trello) because everyone seems to have a favorite, and they all seem reasonably decent. I use Trello for my personal task tracking. I wouldn’t spin too long trying to ascertain which one of them is “best.”

Again, if your choice of a new web app (etc.) to add to your startup’s tech stack is not going to make or break your business, don’t over-index on it. Do some quick research. Get together a couple or a few ideas. Do a brief analysis and review. Pick one and turn back to the activities that are going to be far more impactful on your organization and its success.

That’s the benefit of having a list like this. I hope it helps.

Top Startup Tools

Product Description Other Options
1Password Password management and security
Guideline 401(k) providers Human Interest
Ahrefs Ahrefs for SEO analysis and backlinks; AlsoAsked for keyword analysis on competitors and search term difficulty Also Asked
Airtable Collaborative work management
Amazon AWS Cloud computing
Apollo List building from search critera. Send sequences. Consider checking out new kind on the block Unify Unify
Arc Tech Treasury services
Bill.com Billing and financial automation
Brandpad Brand development and management
Brixx Financial forecasting and planning software
Carta Equity management and valuation, but watch the latest news about them Pulley
ChatGPT AI platform to help with a little bit of everything
Clay Import lists and enrich them (more options than Apollo). Consider also checking out newcomer Unify Unify
Clerky Legal and compliance solutions (company setup)
Clockify Time tracking
DailyBot Slack stand-ups
Deel Global payroll and compliance. Deel is an EOR
DocSend Document sharing and tracking (for a fundraising, DocSend + Dropbox or Google Drive + Google Sheets for tracking)
Docusign Electronic contracts
Expensify Expense management and tracking Tentative: Float (Canada)
Figma Design and prototyping
Flowster Workflow automation and processes
Freshworks Customer engagement and support software Zendesk
GitHub Software Engineering version control and collaborative software
Google Analytics Website analysis Hotjar
Google Workspace Collaboration and productivity tools (email, storage, etc.) Dropbox (storage only)
Grammarly Communication assistant including AI support
Greenhouse Recruiting and applicant tracking Breezy Recruitee
Gusto Payroll, benefits, and HR services. Rippling has a PEO option Humi (Canada) Rippling (US and Canada)
Hubspot Customer relations management (CRM)
Indinero Bookkeeping service. The Bench recommendation is tentative Bench
Intercom Customer messaging and support
Jenkins Open-source automation server for continuous integration and delivery (CI/CD)
Gusto Payroll, benefits, and HR services Humi (Canada) Rippling
Linear Issue tracking and project management
Loom Video messaging
Mercury Banking for startups and businesses. Consider Mercury credit card too Bluevine
Microsoft Azure Cloud computing platform
Microsoft 365 Productivity apps (still use them as good as Google is)
Miro Online collaborative whiteboard Excalidraw
NeverBounce Stand-alone email deliverability solution
Newfront Insurance brokerage Founder Shield
Notion Collaborative workspace for your organization
Okta Identity and access management
PaperStreet Investor updates
Pave Compensation information for startups
PitchBook Data and research for private investments
Quickbooks Cloud accounting software. Also hearing increasingly about Campfire in this category Xero
Ramp Corporate card and services. Brex may not be an option for smaller startups American Express Brex
Segment Customer data platform
Secureframe Compliance and security automation
Slack Team messaging
Stripe Online payment processing and business tools
Supernormal AI tool for meetings
User Interviews Customer research
Vouch Business insurance. Also Embroker Zen Insurance (Canada) Hiscox
Voxer Team audio messaging
Webflow Website design and development
WeWork Co-working (in bankruptcy but still operating)
Wise Foreign exchange
Yubico Hardware security keys
Zoom Video conferencing

While the companies aren’t vetted, another interesting place to search for potentially valuable services is the Y Combinator community of companies.

If you’re a startup CEO or founder, and you feel it would be interesting to chat, I’d love to connect. Learn about my services and please reach out.

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