7 Questions to Best Support Founders

Posted by: Paige Craig

Posted on 04/26/2023

7 Questions to Best Support Founders

Over the last 15 years, I’ve funded visionary founders building everything from robot delivery fleets to web3 creator economies and everything in between. Excited as I was by every new venture, I quickly realized that—like our founders—expertise in every moving piece of the now 150+ investments was impossible and tactical advice was not Outlander VC’s role to fill. So instead, we learned to ask the right questions to support our founders in forging their way into the unknown.  

First and foremost, founders must identify their startup’s North Star Metric, i.e., the #1 most important metric in the business. Then, build a plan that ladders up to their target NSM, including sub-goals like product roadmaps, hiring plans, operational optimizations, sales/marketing strategies, etc. Learn more about defining your North Star Metrics here

With a target North Star Metric and plan in place, here are the seven key support questions we ask our portfolio founders to ensure they prioritize their startup’s success:

First, establish the financial baseline:

  1. What’s your monthly burn and current runway? Burn and runway will impact how to prioritize every subsequent element of the business. As such, we always ask this question first to establish the baseline health of the company and to contextualize the appropriate priority and timeline for the following questions.
  2. What goals do you need to achieve to raise your next round? Do you have the runway to achieve those goals? Building on #1, founders should always be laying the foundation for their next raise. By establishing what must be accomplished before the next round, founders can adjust their short-term targets to reach their North Star Metric and burn accordingly. 
  3. Are you being realistic about your financials? By starting with these baseline financial questions, we can help founders prioritize where their efforts will be most impactful and build long-term success. For example, while “always be fundraising” would be ideal, we recommend founders allow for six months (minimum of four) to fundraise and close capital. Checking in with #1 and #2 lets both the founders and our team better plan for their next raise.

Second, assess operational highs & lows:

  1. What problems are keeping you up at night? This is a great question to gauge not only where the most energy is being spent but also if solving this problem aligns with achieving the startup’s North Star Metric. Once you contextualize pain points within long-term goals, it’s easier to prioritize each problem against your North Star Metric strategy.
  2. Are you on track to achieve your target North Star Metric? Do your “wins” support your target NSM? Not all “wins” are created equal. Keep the conversation focused on how each win drives their target North Star Metric. Things aren’t “working” if they haven’t launched, just launched, or haven’t dramatically moved toward their target NSM. For early-stage startups, we are looking for big wins that demonstrate traction, not minor optimizations.

Finally, asses team performance:

  1. How is the current team doing across character, work ethic, and results? One of the most common founder pitfalls is hesitation around firing “bad fits.” To keep this front of mind, founders should regularly assess each team member’s work ethic, performance, and character, too. While deliberating if the situation is “bad enough,” an ineffective or inconsistent team member can make or break your startup’s success.
  2. How is the team evolving? Are you finding the right people to bring on? On the flip side of #6, scaling your startup will require growing your team, too. Hiring is another pain point that can hinder a startup’s ability to scale, and a founder who cannot inspire others to join them indicates they may need additional support from our team. 

Much like the parable of teaching a man to fish, the best way to support your portfolio companies is not by prescribing tactical advice. Instead, asking these seven key support questions at least once a month trains founders to keep them front of mind as they prioritize their team’s efforts to maximize their startup’s success.

Paige Craig

Managing Partner, Outlander VC

Paige invests in brilliant founders from across the US, using his Outlander Founder Framework to drive returns in the top 5% of VCs globally.


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