Why Startup Founders Need Thinker-Doers for Their Teams

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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.

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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

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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.

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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.

50 Top Apps, SaaS Solutions, Services and Sites 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.

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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.

When Don’t You Need a Fractional COO Like Me

Photo by Linda Eller-Shein from Pexels.

In case this is your first visit, 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.

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There is no right or wrong reason to want to build a business. Maybe it’s a creative outlet for one person. Someone else might be obsessed with solving a nagging problem they observed out in the world. Perhaps a third person never fit into a traditional corporate job and has a ton to offer in a role and company of their own making.

Business building is about changing the future.

A successful new business makes the world different than it is today, and I’ll be a match for anyone who aspires to have a huge positive impact on the lives of their customers and stakeholders.

This brief post is not about all that. It’s about when it might not make sense to work together formally, even if we are a match regarding outlook and values. You can still try me, but I may not be a fit in either of these two situations.

Situation One

You’ve got all the right team members with the right skills and experience in the right roles. You’re not struggling with scaling yourself, and you’re not missing any key capabilities. You have plenty of time to learn what you need to know. You are only spending time on the activities you alone can do. The team has everything else covered.

AND

The organization is learning quickly and efficiently. You have demonstrable evidence you’re onto a compelling new business opportunity (i.e., traction). You have practices and processes to surface the big assumptions and unknowns you need to test or get clarity on to move the business forward. You’re not struggling with team alignment or direction. You are sure about your next moves.

Read also: Overlooked Traits of Successful Startup CEOs

Situation Two

Your team makes you feel superhuman. You’ve eliminated all the significant unknowns relating to the business. Moreover, you’ve built the supporting infrastructure to scale. These efforts are going smoothly. You are making incremental business improvements. You are not making major shifts. You are not feeling out of control. You’re clearly well on your way to building a successful and sustainable business.

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

Congratulations to you for all that you’ve achieved so far. It is a real feat.

If you feel like you fall into Situation One or Situation Two, and there are still aspects of the business or your work life that you want to change, I’m always happy to chat. I’m also glad to be in touch purely for information sharing and networking purposes.

How Startups Can Make the Best Use of Lawyers

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.

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If you’re spending a ton of time and money on legal management, that’s probably too much. But little to no time or money at all is probably not enough.

In this post I’ll lay out a simple tried-and-true framework startup CEOs and founders can use to help you decide what kind of legal advice and support you need to keep your legal house in order and avoid pitfalls that will slow the company down.

The typical startup requires responsive and informed legal advice and a flexible and lean framework for getting it. I won’t dwell on the first two points. This is not the time to have your uncle who does real estate law draft and negotiate your $8 million Seed-round financing documents. And you’ll go mad waiting to hear back from a sloth-like advisor when the business is not yet breaking even and every second counts. Enough said.

Read also: Axiom: Discovering the Benefits of Fractional Talent

At my prior employer Axiom (a venture-backed innovator in the legal space), we collaborated with the General Counsel of Fortune 500 companies to restructure and reorganize the work of their legal departments. The same basic principles offer an excellent framework for startups that can evolve as the business grows, from the early days through Seed and Series A financings and beyond.

Check out the three-step approach and an example of how you might organize your legal operations.

But first, legal AI is captured in the model under “Alternative Model Providers.” This category captures any alternative to traditional law. Watch this space. There’s no doubt in my mind that legal AI specifically will be moving from the Efficiency category to the Experience category over time. It’s just a question of how fast.

Legal Services for Startups (embedded) by John Gauch

Additional factors to consider:

• Account for the complexity and costs of coordinating these legal activities. Theoretically, it might be more effective to split up projects among three tiers of providers, but if that’s going to add a ton of overhead to your operations, you might want to keep it to two.

• A single project can be split across multiple categories. For example, you need an immigration visa for a new team member. Your Chief Financial Officer or Chief Operations Officer is comfortable navigating complex regulatory schemes. One of them might prepare the visa application, and then you could have an immigration lawyer review it to make corrections and suggestions.

• There are functional and emotional elements to the decisions you make in building your framework. Let’s say you’re the CEO of a post-Series A company. You have several top-tier VCs in your cap table and have blown past the $10M revenue mark. For your bet-the-company matters, you may want to select an AmLaw 100 law firm with startup credentials not only to benefit from their expertise and infrastructure. You may also choose them to benefit from their brand and the imprimatur the firm brings with its counsel and work product.

From the beginning of your company’s life, pay particular attention to company formation, founders’ agreements and equity matters generally; intellectual property (IP); and fundamental regulatory and compliance issues. To take one specific example, having people sign confidentiality and IP assignment agreements is critical. If you neglect ongoing corporate formalities, you might be able to fix that up later, but it will be a nuisance, and it could lead to problems—if you were to issue more equity than you have authorized, for instance. Commercial agreements might fall in any tier of the framework above, depending on your business and the individual transactions, and should be treated accordingly.

Read also: Navigating Startup Fundraising: Insights from an Experienced COO

There’s always a chance a legal issue can arise that knocks your startup journey off track. Still, a proactive and reasoned approach to handling legal services can optimize the quality and cost of the advice you receive--improving the odds of long-term startup success.

Use the illustration above and consult your trusted legal advisor(s) to devise a legal management strategy specific to your company and its lifecycle stage.

I’m always happy to chat about how I help startups. I’m also glad to be in touch purely for information sharing and networking purposes.

Nothing in this blog is intended to be a substitute for legal advice from an attorney knowledgeable about your unique situation.