StartUp Advisor Topics

So What Happens?

The largest question every one has when they consider a coach – aside from believing they are invincible and don’t need help, or looking for a magic unicorn to solve their problems, is how does it actually work, how does a conversation convert into value. For the founder, for the company, for the customers?

Generally the first call is a lot of listening and asking questions, the how, the why, the when, the what, trying to understand how you think, strategize, execute and also how you like to communicate. Often within call, you will provide glimpses of struggles you know of, and struggles you don’t, you will highlight your strengths and your excitement and potentially lay out your vision (short or long term).

I am not a therapist, so whilst it might seem fantastic to get so much off your chest, and perhaps a glimpse of some of the areas that scare you, the key of the first call is to listen and try to prioritize the areas of focus. That priority might be because you have a massive customer opportunity, you are about to raise a bridge round, your processes are too manual, you are too overloaded, you are doing shit you hate, you have not taken a breath to understand how to measure, understand and take action on your data. Whatever it is. Where do we start, sometimes accretive value doesn’t have to be this massive thing, it might be saving you 20 minutes a day, it might be implementing a process so you are no on call if the servers go down. Happy, excited, passionate founders, doing what they love generate great companies, so the focus has to be first on you, as a founder and the outcome is what benefits your business.

Some first calls we jump straight into go to market, business development methodologies, customer education and awareness and balancing it all with a razor thin budget. If part of the value you need is someone to bounce ideas off and get honest and objective feedback, great.

The StartUp Advisor wears so many hats, because you do. Some calls have a clear agenda, others allow for fluidity, learning what works best for us as a team is the first priority.

In almost all the conversation themes, you are the person most knowledgeable, you are the center of your companies universe so jumping between topics is natural.

Consistent Conversation Themes:

The Technical Conversation

Almost always, whether the founder is technical or not, we have a broadly technical conversation. The conversation itself might not be technical (unless you are), but they are functional business questions you should be prepared to talk about. You are the CEO/Founder – you have an obligation to understand how your product is built and delivered.

There are a few critical reasons why this often comes up early:

  • Are you prepared for corporate governance requirements associated with selling into large enterprises? (CSA)
  • Are you thinking about certification of your technical & business processes (ISO/SOC2)
  • Have you considered entering the Government Space (NIST 800:53)
  • What does it look like to whirl up a new customers?
  • What does it look like to go from idea to production?
  • What does your DevSecOps stack look like?
  • What processes or systems do you have to ensure availability?
  • What type of reporting / analytics do you see / care about as it relates to your technical delivery?
  • What is your solution architecture and how does it provide future proofing as you iterate or pivot?
  • How are technical decisions made?
  • How do you evaluate build vs buy?
  • How technically organized is your organization (Tribal Knowledge / Permissions / Founder Control)

The Product Conversation

I am deeply interested in understanding your product, the problem it solves, how that problem is communicated, and ultimately how its fit in the market will lead to customer growth. The key themes we often touch on:

  • How does your product roadmap work, whats the process?
  • Is everything always an emergency or do you have relative cadence and planning?
  • How do your customers participate or gain transparency into your roadmap?
  • What is your release management look like, including support, education & communication?
  • How do you way the differing ideas / tickets / features / functions against each other?
  • How do you communicate bad news to your customers?
  • How much are you overselling?
  • How behind on your roadmap are you?
  • What functions of the technology bring the most value to the user/customer/company?
  • How do you flesh out the requirements of your new features/functions?
  • How do you measure the success of a released feature/function?
  • How is product knowledge scaled internally/externally?
  • How do you enable customers to be successful out the gate with your platform?
  • How to you intake feedback?
  • How often are you talking to customers?
  • Are you a feature factory of a value creator?
  • Do you prioritize internal product value engineering (development / success efficiency)
  • How do you measure product health?

Go To Market / Customer Acquisition

  • Who are your customers?
  • Why are they your customers?
  • How did you find them?
  • Do you measure CAC?
  • How are you managing pipeline?
  • How are you presenting and converting from interest to purchase?
  • What channels are working?
  • What methods are you utilizing?
  • Are you dominating in thought leadership?
  • Do you have a media/press/analyst strategy?
  • How are you marketing as a business, a product, as individuals?

Customer Success Framework

  • What is the customer journey from pre-hello to live on your product?
  • How do you manage training, self service, support?
  • Do customers know how to be successful? (Are they?)
  • Does your product actually solve the problem?
  • How do you measure and report success (Vanity & Sanity)
  • What data do you look at to understand customer health?

The Company, People & Money

  • Defensive strategy?
  • Organizational structure?
  • Understanding financials?
  • Fundraising & Investor Reporting?
  • KPI / ROI Tracking
  • Organizational Compliance
  • HR / Policies / Guidelines
  • Learning / Education
  • Hiring Roadmap
  • Your Exec Team
  • How You Consume Information
  • How your employees are tied back to your core success metrics


  • What does your day look like?
  • What is your role?
  • What do you love / hate?
  • What keeps you up at night?
  • How do you prioritize?
  • What does your support framework look like?
  • Are you financially stable?
  • Are you healthy?
  • Do you have key man insurance?
  • Do you have a succession protocol?

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