Building Your MVP as a Non-Technical Founder

I did a presentation this week at Coloft that looked at how Non-Technical Founders can go about getting their MVP built.  It had a passionate group of 50 people attending.  I promised to do this post as a follow-up to the session to provide additional links and information.  It should also give a sense of what I covered to people who were not there.

Here is the outline of the talk and some links from prior posts that talk to the issues that I discussed in the talk.

Purpose of an MVP and Defining the Right MVP

I've really not talked as much about this in my blog even though its hugely important.  I generally hear the following as reasons for founders building their MVP:

• I need it to get investors interested (NOT VALID)
• I need it to see how early customers use it to get feedback (RARELY VALID)
• I need it to test/prove aspects of the product such as (VALID)
  • Cost of Customer Acquisition
  • Conversion Rates / Pricing
  • Viral Coefficient

My claim is that the first bullet, although extremely common, is a misguided reason to build the MVP.  Investors my tell you that, but what they can look at your product on paper and tell what it does and they will understand if it can be built.  Once you build it, they will now ask you about the key metrics that they need proven in order to see if you really are a good investment.

The second bullet, getting feedback from customers is most often not valid either.  Again, putting something down on paper (wireframes, graphic comps) and getting feedback from potential users can tell you most of what you would learn from a working MVP.  There are a few cases where you somewhat need to see the system operating to have a sense of the value.  Examples might be a recommendation engine, search engine, matching engine or something with a complex interface.  Even with these, you will have paper-tested your MVP, but the reality is that customers will not be able to assess the value to them until they actually use it. 

The real reason to build an MVP is to do early tests of key Startup Metrics for the business.  To prove/disprove a hypothesis.  One of the questions in the session was "How do you know what to put in your MVP?"  Once you have the metrics defined, it focuses your effort.

Ways to Make Your MVP More Minimum

We spent quite a bit of time talking about a complexity scale and the kinds of resources you can viably use at different levels of complexity.

Simple MVPs get built with less the 3 Programmer Months worth of effort (that's 3 months a single programmer working full-time).  More complex MVPs are going to be 12+ Programmer months.  There are some MVPs that are unavoidably complex.  eHarmony for me fell into that camp.  We needed the matching algorithm.  Many MVPs can be made to be very simple.

• Paper Prototype or a Smoke and Mirrors Prototype - you can just build something on paper or even just one that you can click through and get a lot of the feedback you need.
• Fake Site - you can have what looks to be a real site, even take "orders" but not actually have anything able to run it.
• Leverage Existing Platforms or Third Party Products - you want to test your social network, grab Drupal and whip something together, or even just use a hosted service.
• WordPress - we spent quite a bit of time talking about how you could do a lot with WordPress to provide simple forms of lots of functionality.  WordPress is pretty easy to hack.  And the back-end is something that a non-technical founder can manage.  We end up using WordPress a lot as the marketing front-end of our web sites.

The bottom line is that you should first look to make your Minimum as Minimum as possible.

Here are some important and relevant posts that relate to the topic of defining the right MVP.  The "Questions" post is probably the most important. 

• Don’t Subtract - Restart to Find the Minimum Viable Product
• 32 Questions Developers May Have Forgot to Ask a Startup Founder
• Startup Software Development – Do Your Homework Before You Develop Anything
• Document Your MVP for a Developer

What Do you Need to Get Your MVP Built

From the graphic above, you can see the kind of resource you might need to be able to build your MVP.  If you are on the lower complexity end, the key is defining small chunks of work that can be done quickly by a developer.  If you do not break it down into small pieces, its hard to make progress with part-time resources, freelancers, etc.

• Equity-Only CTO and Equity-Only Developers
• Technology Roles in Startups
• Want to Know the Difference Between a CTO and a VP Engineering? (someone asked specifically about this)
• Hiring a CTO for Your Startup

Founder / Developer Gap

I've spent a lot of time on the Startup Founder Developer Gap and knowing what you need in terms of a Startup CTO or Developer. 

In this talk, we spent most of our time on Technical Advisors: Every Web/Mobile Startup Must Have One and how they should be helping you:

• Specify the right things to be built. 
• Third party products are used appropriately.
• Structure development contracts appropriately or directing the in-house team appropriately.
• Plan for past the initial MVP.
• Review the code being built.

Finding and Selecting a Technical Cofounder / Developers

• How to Hunt Programmers for Your Startup - A Field Guide
• Finding a Technical Cofounder for Your Startup

Development Challenges

• Startups and a Common Misunderstanding in Agile Software Development
• Poor Software Developers - Pull the Plug Early
• Symptoms of a Weak Development Team

Technology Choices

Choosing a Programming Language and Framework for Your Startup

 

Finally, if you made it this far, then take a look at: Free Startup CTO Consulting Sessions.  I'm always happy to try to help startups figure out how to go after creating their MVP.

Startup Mentors

I've had several Startup CTO Consulting sessions recently where it became apparent that the Founder needed help with the business and product as much or more than the technology.  I suggested that they should look for someone like me, but on the business end.  Then we discussed how they could go about finding this startup business advisor.

Then I got an email that asked:

I'm leading the marketing efforts for an early-stage startup.  I recently completed an MBA, which I feel gave me a good basis in the fundamentals of building our brand from the ground up. However, I often wish that I had someone more experienced both in marketing and working in a startup environment that I could go to for advice. Do you have any suggestions for how to find a good mentor?

Great question and I believe that just like finding a Technical Advisor for your startup is critical, finding a good mentor is critical.

Mentor vs. Advisor

Generally when I talk about startup mentors and advisors, I distinguish them in terms of:

• Mentor focus is You: 
  
  The marketing person above is looking for someone to help them with their personal challenge.  They want someone who understands their current role and can help them be successful there.  They will also be concerned about how this leads to their next role.  They may open doors to the next role.
  
• Advisor focus is Your Business:
  
  The startup founders need help with the business and I'm advising them to find an Advisor who will focus more on the business then on them as a person.  They likely want someone who knows the industry and can open doors that can help the business.

These are not mutually exclusive and good mentors and advisors get into both. 

Finding Potential Mentors

You are looking for someone who is

• A couple steps ahead of you in progression
• Have worked in similar roles in similar kinds of companies
• Local to you

For example, I'm looking for a marketing professional who's worked at a couple early-stage startups ideally one of these is B2B selling to advertisers and is located in Los Angeles area.

You should begin asking at networking events and people you know in the startup world.

For me, I'd use LinkedIn.  The challenge is that LinkedIn is not that great with finding people who were at early-stage startups.  So the way I would do it is to find examples of specific startups that have grown up locally and who marketed similar to how you plan to market.  Then you search for the people who were in marketing there early on.  Likely they've progressed, so it may be a pretty natural fit.  This can take some work, but its worth it.

This also avoids a common problem that will sometimes happen when you go the networking route.  People will suggest folks who are high profile.  They regularly speaks at conferences, used to work at Google, and have other similarly impressive aspects to their background.  That may sound good, but that doesn't make them a good mentor. 

Have they worked in similar kinds of situations?  Most of us are not Google.  An early-stage startup is a different animal.   From Why Every Startup Founder Needs a Mentor - And How to Find One

Don’t just fall in love with someone’s reputation, perceived celebrity or name. Identify someone who could be directly relevant to what you want to do, or who is pursuing a similar vision. And someone who is likely to have the time and the inclination to help you.

Mentor Progression

To me this is a complex problem, it's a bit like dating/marriage.  You are the person who wants to commit but you have no idea if the other party is going to be willing to commit to you. 

I don't believe that you should go out saying to a potential mentor that you are looking for a mentor.  While that's open and honest, you know how it works out if you bring up commitment too early.  And I'm not alone.  In How to Find and Keep Your Ideal Mentor:

Once you’ve identified an ideal mentor, you need to create the relationship that houses the mentorship. Here’s a little secret about finding mentors — nobody has time to mentor you. And they probably lack interest initially. If you’ve ever sought out mentors, you’ve probably found that many of them were reluctant to make the commitment and ran when they heard the word “mentor.”

So, where do you start?  For me, its coffee?

Can I buy you a coffee and talk to you about my challenges?

Or in the case of the LinkedIn outreach:

Hi John,

I'm leading the marketing efforts for StartupRoar, an early-stage startup that sells to B2B advertisers.  We are doing well, but have some interesting challenges.

It looks like you were in a similar kind of role at XXX and you likely had some of the same challenges. 

Would you be open to getting together for coffee and talk about my challenges and how you addressed them before?

Thanks,

Tony

If you are working on something interesting and you ask nicely, there are a lot of people who are willing to have the conversation.  And sometimes that grows into more conversations.

If you've talked to a bunch of people and no one is willing to get coffee with you, then that's a sign that you are working on something that's not interesting or you've not done your homework.

At the end of your first coffee, if things have gone well, I like to say

This was great.  I really appreciate your time.  I've got a lot of great ideas and things to do.  Would you be open to getting together again at some point as I continue down this path?

That's right, you begin to set up your second date right at the end of your first date. 

Accelerator / Incubator Mentors

Most accelerators and incubators have a long list of potential mentors.  I'm a mentor at Start Engine and Founders Institute LA.  I want to warn you that just because you are going into one of these programs doesn't mean you will find a mentor.  It means you have easy access to people who could become a mentor.  You still have to do the work of connecting with these people and turning them into an actual mentor.

In Startup Mentoring, The Socratic Way, Fred Destin tells us:

The faster you can get past the pitch phase ("let me convince you that my idea is great")to the constructive phase ("let me exchange with you to make this thing better"), the more benefit you will both derive from the interaction.

I've been in lots of conversations where the founder is just pitching me.  This happens a lot at the incubators / accelerators.  I'm thinking I'm in the meeting trying to help.  All we get are pitches and most often there's not opportunity for a startup to say, "I could use some help with X."

We all have challenges - lots of challenges.  Be open about your challenges, especially when you are talking to a potential mentor. 

You still need to tell them about your challenges and start with a meeting/coffee.

Let me stop here, because if you are in a program like this, then just go over to Ben Yoskovitz's post How to Maximize the Value of Mentors in Accelerators.

Do Your Homework

I worked on a startup project with Stedman Graham and when he was doing a presentation for a group of teachers, he said something similar to this CNN interview that really stuck with me:

Everybody's equal because we have 24 hours. The question becomes, "What do you do with your 24 hours?"

He's talking about making life choices, but anyone who's worked in a startup knows that there are always a million things to do and we constantly make choices about where we will spend our time.

The same is true of your advisors and mentors.  So show respect for their time by doing your homework before you ask them questions.

I wrote about this a long time ago in Questions Before You Ask.  In that case, I was talking about the homework you should do before you reach out through LinkedIn for a question. 

There's a ton of information out there, so if you have a particular situation, make sure you've:

1. Searched for Answers
2. Keep a List of What You've Found
3. Read through What You Find
4. Compose What You Find Into a Preliminary Answer
5. Figure Out What the Real Question Is
6. Ask the Real Question

If you are asking your mentor questions that shows you've not done your homework, you will likely lose access to that person's time.  They will push you to do your homework the first time.  The second time, say goodbye.

Additional Resources

• Venture Hacks - Advisors Series
• Finding (And Keeping) The Right Advisors For Your Business
• What is a Mentor Cycle
• Mentoring the mentors: Advice and inspiration for startup mentors
• How I Try to Mentor Startups (And Hopefully Add Value)
• Mentor Manifesto
• Find and engage great mentors
• Startup Mentoring Sessions - How to Get the Most Out of Them

Document Your MVP for a Developer

I was talking with an early-stage founder who has a product vision and wants to get a Minimum Viable Product (MVP) built.  He is not a technical person, but is somewhat web savvy.  He wanted to get input from me on what he's doing, and he wants to begin to ask developers what it would take to build his product.  I asked some of the same questions I ask in my Free Startup CTO Consulting Sessions and then I get to a very common conversation:

Me:  Do you have specs?
Founder:  Ummm ... <embarrased look> ... what do you mean?
Me:  Product definition, use cases, feature list, wireframes, comps, really whatever you have.
Founder:  Umm ... <still embarrassed> ... what format would you and the developer want that in? 

I'm never trying to embarrass someone.  I know how it feels.  It's the same as when I've created financial models and then have it reviewed by a hard-core CFO, sophisticated investor or similar kind of expert.  And in the case of defining mobile/web/software, there is even more variability in terms of form and format.
So, I promised this founder to do a post talking about how you go about create specifications of your MVP.

First Relax

Before you begin reading all of the stuff below, it's going to be new, different, confusing.  You likely are writing your first one of these.  Don't stress over format.  Don't stress if you are doing it right. 
This should be an iterative process with advisors and customers providing feedback on the product. 
Conversations with a technical advisors or possible developers should be iterative. 
In fact, let me provide an important warning:

If you create these documents, don't have input from a technical resource, take it to a development shop and they provide you a price.  Go find a new technical resource. 

So, just get down what you can in a form that works for you.  I don't expect you to provide all of these things.  Part of what I like to find out is where you are relative to capturing these things.

Business Concept

The key first part of the conversation with a developer is having a good capture of the business more broadly.  The  business canvas model is a good short list.  Or you can have a pitch deck.   You might also have a business plan, marketing plan, financials, competitor analysis or other kinds of background document.
Ideally you are also able to say what you are really trying to prove to get to the next level.  For example, if you are trying to determine viral coefficient (see Startup Metrics), then the focus should be around those aspects of the MVP.  It's important to know where the business is today and what you are really trying to achieve.
Quite often these things get old quickly.  It's fine to send out documents that have older information.  Just make note of it in the document and/or in an email when you send it.  Seeing the evolution of thinking is not a bad thing.

Customer Development Notes

I'm assuming founders are having customer development conversations.  It would be great to get notes and summaries from these.  See also: 12 Tips for Early Customer Development Interviews, 12 tips for customer development, tips for customer development.

Prioritized User Stories

Define the customer problems and beginnings of the solution through user stories (see user stories, user story).  Prioritize these stories.
Examples:

• http://www.westborosystems.com/2010/02/user-story-examples/
• http://en.wikipedia.org/wiki/User_story#Examples

Product Feature List

Create a prioritized high level product feature list (see Product Backlog).  Make sure you look at 32 Questions Developers Should Ask a Startup Founder to spark possible additional features.  Make sure you keep focused on your key business drivers and prioritize the features aggressively based on those drivers.
Examples:

• http://www.mountaingoatsoftware.com/scrum/product-backlog-example/
• http://epf.eclipse.org/wikis/scrumpt/Scrum/guidances/examples/example_product_backlog_B6A03674.html

Functional Details

For the higher priority features, begin to capture additional level of detail of those features particularly focusing on the behavior of the application.  See User Story is Worthless - Behavior is What We Need although you don't need your behavior description to be as formal as what is presented.  Really this begins to be a Functional Specification.  Developers don't need everything to be fully documented.  Rather are just looking for more detailed description of the features/functions.
Examples (these are going to be more detailed than you need to get to at this point):

• Sample Spec
• Functional Specification Example

Wireframes, Comps, Clickable Prototype

Create wireframes for a few key screens that sketch your concept using a tool like Balsamiq. 
Send across any graphic designs you currently have. 
If you happen to have a clickable prototype, that's great.  That's fairly uncommon.

Other Documentation

Here are other things you might be told about and try to capture:

• Personas - Examples: http://www.uiaccess.com/accessucd/personas_eg.html;
• Use cases
• Software Requirements

Additional Resources

Here are a bunch of additional resources

• What is the minimum viable product?
• Minimum Viable Product: a guide, Lessons Learned, Eric Ries, August 3, 2009
• 10 examples of minimum viable products
• Minimum Viable Product revisited – the MVP Curve?
• Don't Let the Minimum Win Over the Viable
• Minimum Desirable Product
• How I built my Minimum Viable Product
• The Death of the Wireframe? Towards An Integrated Approach to UX Design

You should definitely look at Steve Blank's book and review his blog.

Technical Advisors: Every Web/Mobile Startup Must Have One

I did a presentation recently for a graduate class from The Founder Institute around getting online/mobile products out the door.  I LOVED it because, the presenting part was over quickly and we got into specific issues that the founders had in terms of getting things built.  It was like having a bunch of mini-Free Startup CTO Consulting Sessions all in one room.  But what was interesting to me was that I found myself recommending that each of them should have a technical adviser.

Why?  Roughly, they needed to make sure:

• Specify the right things to be built. 
• Third party products are used appropriately.
• Structure development contracts appropriately or directing the in-house team appropriately.
• Plan for past the initial MVP.
• Review the code being built.

This is exactly the kind of thing I'm doing as a Part-Time CTO or Technical Advisor for startups.  It just didn't dawn on me how common this need is.  And it made me come to a new realization:

Every early-stage web/mobile/online startup should have at least one technical advisor, probably two.

There are two kinds of advisors that are commonly needed.

Strategic Technical Advisor

Look at the business and determine what's going to make sense from a development perspective in the short-term, longer-term.

They need to be able to know the key Questions Developers May Have Forgot to Ask a Startup Founder, figure out where/when/how to bring on development talent (Hiring Developers Before Product/Market Fit? , How to Hunt Programmers for Your Startup - A Field Guide), how to manage development resources (Startups and a Common Misunderstanding in Agile Software Development, Poor Software Developers - Pull the Plug Early, Symptoms of a Weak Development Team), choosing technical frameworks (Choosing a Programming Language and Framework for Your Startup), and other aspects of making broader choices about what will get developed, how it will be built, and making sure that you ultimately deliver the right stuff at the right time.

I was very worried for several startup in the room.  They were making some significant choices that were going to have lasting impact on their company.  Why do this without the right technical advisor?  Would you create contracts without an attorney? 

Tactical Technical Advisor

There's also a tactical level for technical advisors.  We are producing the right functionality, but is the code that's being produced the right product?  Is this something that's scalable and extensible?  This kind of advisor should be looking at the code on a fairly regular basis to make sure that the team is building the right thing.  This is important whether you are outsourcing or building it in-house.  If you are outsourcing, then this person will also be protecting you from issues like being able to access the source code and making sure can bring it in-house at a later time.  Do you really have control of the development?  If you don't have this kind of person and you are not personally looking at the code, then you don't really have control.

There are some technical advisors who can do both strategic and tactical, but its common to find a tactical advisor separately.

CTO Founder - Do they really still need a technical advisor?

I know relatively few people who are good at both a strategic and tactical level.  Most early-stage, in-house teams needs to be hands on developers, not strategic.  It's rare to find a person who is good at both strategic level thinking and is still a rock star, cranking out code.  Early-on, bring people on who can produce volume.  You can get strategy level on a part-time basis.  I've talked about this before in Startup CTO or Developer.  Is this person a CTO or a developer?  Likely they will have gaps in one or the other.  Get an advisor to help supplement where there are gaps.

By the way, do you know that most development teams use peer review of code to help ensure good development practices.  Who's doing that for your CTO?

Where Do I Find a Technical Advisor

You are looking for part-time people in these rolls so you often are finding people who already are employed somewhere else.  In Los Angeles, I have easy access to a bunch of potential strategic technical advisors through the LA CTO Forum.  If you need a strategic advisor, contact me and I will connect you with someone from the group.  Another avenue is looking for CTOs/VP Engineering via LinkedIn.  It's going to be a numbers game to find the right person that way, but still quite doable.

Tactical advisors are also going to be already developing or leading development full-time at a startup.  They will have the title Lead or Manager.  They should only be a year or two removed from full-time hands on.  Ideally they have experience with your full technology stack, but in some cases, having them learn about best practices will be necessary.

Compensation

This is going to depend on the specifics of the work.  When advisors need to jump in and spend significant hours on a particular issue, then likely cash compensation is going to be required.  If it stays at a few hours per month, then using something like Founder Institute's FAST agreement probably makes sense.  Just make sure its clear what the expectations are going into any engagement.

Why Investors Should Demand This

I quite often get a call where a founder raised $150K of initial money and has spend $120K on in-house or outsourced development and the software is 90% done.  But they are having a tough time getting it all the way done.  As I mention in Symptoms of a Weak Development Team, the number one reason I get calls relates to an old software engineering adage:

The first 90% of a project takes 90% of the time.  The last 10% takes the other 90%.

In the case of these calls where the initial money has mostly been spent, it can be very tough to recover.  Most often the failure is both a result of the founder not doing the right things and because the developer over-promised and failed to ask the right questions.  Having a strategic and tactical advisor can greatly reduce the chance that this is going to happen.

What's funny is that once software has been built and you move from Seed to A or B round, I often get calls by investors about reviewing the existing product to see if it has reasonable quality and if the team is going to be able to continue to produce going forward.   Why a Seed level investor doesn't insist on a technical advisor, I don't know.

Bottom line - if you are an early-stage startup with online or mobile technology as part of your solution, you ABSOLUTELY NEED a technical advisor.

Find and Talk to other Startup Founders of Similar Startups

One of the recommendations I make all the time to startup founders, is to find other founders who have tackled similar problems as yours and talk to them about how they solved these problems.

As an example, I'm working with two sets of founders who are both going to be dealing with Getting Started with a Two-Sided Market Business - they are variants of two sided markets, but have similar characteristics.  They have both chosen to launch first in a particular geography.  Because their audiences are different, they will take very different approaches to how they do their geography specific launch strategy.

My suggestion to both of them is that they should talk to founders (or maybe early employees) who have launched startups with similar characteristics.   You should consider:

• Audience
• Product
• Strategy
• Business Model
• Competitive Set

You probably can't talk to someone at a direct competitor (although ex employees may work), but it is generally easy to find parallel businesses.   Who has launched a similar kind of business?  Ideally they've launched these fairly recently.

So who has launched businesses with local focus initially?   Well, there are going to be a ton of these.  Come up with various ideas.  Ask around about others.  But let's just say you came up with Groupon as one of them.

First Stop CrunchBase

Here's the link to the Groupon Profile on Crunchbase.  Here's some interesting things I can find:

You can find Founders listed here.  Former people can be a wonderful source of information as well.  See below for tracking down these folks through LinkedIn.

Acquisitions and competitors can often yield startups that took similar approach to how they rolled out, had some success.  Worth looking through these for some interesting parallels.  Again look for founders.  And save names of of companies that match your criteria.

Second Stop LinkedIn

Advanced people search in LinkedIn is a beautiful thing.

In this case, I'm looking for:

• Company - put in the related startup
• Title - "founder" or "marketing" or nothing

You will come back with some very interesting folks.   My suggestion would be to not necessarily target Groupon itself, but more of the competitors and acquisitions.  In some cases, you can target people who were at one point at Groupon and now have founded something else.

Once you've found some people, now its time to reach out.  I've talked about this before in LinkedIn Conversations.  Here are the keys:

• Show that you are real and serious.  Funded is a good word to use.  As is being specific about your issue.
• Be brief.
• Ask for a brief conversation.
• Don't use the words "pick your brain"

As an example:

Hi Joe,

I'm the founder of an pre-launch, funded startup that will be doing a couple local launches to get early traction and determine whether our business model holds.  We have some ideas on how we will launch this.  It looks like you've been through this exact thing before for a parallel kind of business so I'm hoping you can help me. 

Would you be open to a brief conversation around this?

Tony

I like to send these directly, but will do it indirectly through an intermediary when necessary.

CMO CTO COO Equity and Compensation

I was just asked about a particular startup situation (seed stage, CMO hire, non-founder) and particularly what compensation and equity is appropriate.  I know a lot more about CTOs specifically CTO Salary and Equity Trends 2009-2011, Visualization of Startup CTO Equity and Salary Data, Startup CTO Salary and Equity Data, but I've previously written about the issues with Equity for Early Employees in Early Stage Startups.

To find the equity numbers that were relevant for the particular person here, I went back through my prior post and looked at

Wilson Sonsini and DFJ Gotham Ventures

The Option Pool Shuffle

Employee Equity How Much

How much equity for investors and employees?

Seed Stage Compensation

What are typical compensation numbers?

Quick & Dirty How-To: Employee Stock Option Allocations

Lead Developer to CTO at a Startup

I received a great question via LinkedIn:

I'm the founding engineer and working hard to launch my startup.  I seem to encounter a lot of people who want to attach a CTO label to me as I'm the only programmer on the founding team of three.  While I do fill that role at the moment, I'm a little hesitant to refer to myself as a CTO as we still haven't launched a product, acquired a single user, or turned or a penny in profit.  I also recognize that while I am the first technologist on the team, I will not by any means be the last and I'm hoping that subsequent hires will be people I consider brighter and more talented than myself.  This leads to a set of questions: 

• What is the role of a CTO in the early stages of a company, and does that role change later on as both the company and that individual matures? 
• What can I do to best equip myself to step up when the need to officially fill this role arises? 
• How will I know when the need has arisen? 

I've previously addressed the role of a CTO in early-stages in my post Startup CTO or Developer.  It specifically answers the first questions about role and how it changes as the company matures.  For example it includes the following kinds of things that a CTO should be addressing, but that may not be part of the expectation, time allocation, etc. for a Lead Developer:

• How much will it cost to build what we need to build?  How can I control costs but effectively get stuff developed?
• How can we phase development to balance cost, features, risk, etc?
• What options do we have?  How do we balance those options?  What makes the most sense for us?
• Given likely market changes, how will we design and build so that the systems can respond to marketplace changes?
• How do we need to structure the systems to get ahead and stay ahead of the competition?
• What are the biggest areas of technical risk?  How can we address this risk?
• What technology research is required?
• What technologies will we use?  What existing systems will we leverage, what programming languages, software development methodologies, web application frameworks, revision control systems, etc.?
• What other kinds of systems will we likely need?  Accounting?  Reporting?
• What are the important security considerations?  How do we balance concerns vs. cost?
• Where are the likely future integration points with other systems?
• What areas of the application are likely sources of scalability issues?  What kinds of spikes in traffic could we have?  How will we address these without significant cost?
• How are we going to manage the product roadmap?  Make sure we make short-term progress, but not at the expense of longer-term objectives?
• What do we build in-house or outsource?  What parts might we do off-shore, on-shore, in-house?  What does the staff need to look like over time?  When will key hires come on?
• What other kinds of capabilities such as graphic design, user interaction, product manager, QA will we need?  Who will do that?  Who’s responsible for what portions?
• How will we find and interview developers? 
• How do we motivate and manage developers?
• What do we need to do to make sure we can survive technical due diligence by investors and partners?
• What specific technical innovations might make sense?
• What can we build that might be protectable?
• What metrics are going to be the key startup metrics and how do we get those metrics without too much cost?
• Where and how will we host the systems?  What’s our purchase, licensing, SaaS strategy?
• What other CTOs can I ask about complex questions to see how they’ve addressed these issues?

If you are a Lead Developer now and want to grow into a CTO role, there's some good news and bad news.  The good news is that many of the founders that I talk to who are trying to find the lead developer want someone who can grow into the CTO role.  The bad news is that there are a couple of things working against you making the transition.

Startups tend to focus on immediate development needs, getting product out the door, and are often short-sighted.  Then the Founder/CEO and the investors wonder why the above questions are not being addressed.  They attribute it to lack of knowledge and skills rather than focus.  Result => "We need to bring in a CTO."

Startups either grow or die.  If the startup lasts into a few rounds of investment, the rounds get larger, and the team grows.  A skills gap will emerge.  The lead developer who's used to leading a team of 3 will have a much different job trying to lead 40.  In fact, it's likely the case that it's better to keep the lead developer leading a small team to get product out the door.  It's also the sad fact that there's often a desire to bring someone in who has a bigger reputation and likely experience with larger startups that have gone through M&A or IPO.  Again, both of these will lead to => "We need to bring in a CTO."

There are definitely cases where the lead developer grows into a CTO.  However, I will say that there are MANY cases where the initial lead developer does not turn out to be the CTO of the series C/D startup.

What can you do to position yourself to make the transition?

Here's a dirty secret about most startups.  Unlike some larger, more mature organizations, most startups don't spend much time or effort helping grow their employees beyond the immediate needs of the startup.  Whatever the startup needs in the near-term is what the focus will be.  When they recruit you, they should tell you about what you will learn, but it will be focused on technologies and skills that they immediately need for the success of the business.

In the world of startups, it's critical that each person takes responsibility for managing their own career.

But that's most often not the case.  In How to Level Up in Your Career as a Startup Software Engineer, Pete Soderling points out something that's a bit of a dirty secret in the world of startups:

Many startup software engineers don’t take proactive steps to manage their careers.

Learning, Networking, Mentors

From the question, this person is clearly looking at the issue of how to grow into this role.  Likely one of the bigger challenges is simply not knowing what you don't know.  Towards this, I believe you need to seek out continuous learning opportunities.

If you are the senior most development leader, often there are organizations locally that you can get into where you can meet peers.  Here in Los Angeles, it's the LA CTO Forum - a private, invite only group of 250+.  The brain power of this group is amazing.  And it's quite common for people to get together outside of meetings to discuss issues they face and/or to seek a kind of mentoring relationship.  Finding an informal mentor or two would be a great way to be able to continue to focus on this and make sure you are caught unaware.

This group may be a bit unique, but in every geography there are lots of industry and technical organizations where you can seek out similar kinds of people.  You could even use LinkedIn.  I believe you will find lots of CTOs quite willing to help you as a mentor.

In addition to networking, I would suggest that formal learning is a great idea.  This can take the form of a local university, online courses, going through relevant books, etc.  The key here is to begin to avoid technology specific content and instead focus on management skills.  This is likely your bigger gap.

If you are seeking to ultimately be the CTO of a larger startup, it may make more sense to join an existing larger startup and learn from that CTO.  The size of the startup makes a huge difference in terms of the challenges the CTO faces. 

Make sure you are continuously looking at the business and customers.  Get in front of customers as often as you can.  Engage heavily on the business and product.

Allocate your time differently so that you focus on the issues that a CTO will be looking at:

• strategy
• communicating options and influence rest of leadership team
• build/grow/direct/motivate team
• financials/budgets

You'll note that a lot of the skills and focus of a CTO are around communication, business, management, team.  This is often a major factor in determining that transition.

I'd be curious what other advice people have.