Startup Execution, Startup Talent

Nailing Your Fantasy Draft

Fantasy sports leagues have flourished in the last 10 years. I love football, but since I lack the size and skill to play in the NFL, I have to settle for vicarious competition in a fantasy football league. Anyone who does well in their fantasy league knows that the key to success is having the right players on your team. Getting the right players is all about nailing your draft picks and paying attention when quality players are available.

Your startup is no different. In my experience, getting the right players is so important that I have devoted several other articles focused on this topic, from building the right interview processes and skills to the role of game changing team members. Here, I have a few recommendations that will help you identify quality team members.

Show, Don’t Tell

Most interviewers are satisfied if the candidate tells you about their past exploits. It’s certainly important to get an overview of the candidate’s past work, but it’s vital to have the candidate show you their skills. This “show me” philosophy is the foundation for the hackathon, a popular Silicon Valley recruiting tool (which was immortalized in an over-dramatized scene in The Social Network). Although not as glamorous as Hollywood would have us believe, this “show me” exercise is still a very important part of identifying true skill. If you are hiring a pro services consultant, have them write a SOW. If you are hiring a programmer, ask them to write some code as part of the interview. If you don’t have time to create a programming exercise relevant to your startup, at least use a generic problem from a site like

My fourth startup was heavily dependent on a team of very strong Cisco network engineers. Every engineer we brought in for an onsite interview had to demonstrate their hands-on knowledge with real Cisco gear. We set up lab with a laptop connected to a Cisco firewall, which was then connected to a server. We then asked the candidate to configure a pinhole and NAT for web traffic from the client to the server. This is a simple exercise that a seasoned Cisco command line engineer should be able to do in 10-15 minutes. The candidate was provided with access to Cisco manuals if needed. I was shocked how many Cisco Certified Network Professionals (CCNPs) — a mid-level certification that can be roughly described as a “Bachelor’s degree” in Cisco technology — were unable to complete this simple exercise, even after laboring for over an hour.

If they succeeded, we gave them a second, more difficult exercise. We asked them to configure two separate VLANs on a switch intended for a production network and demonstrate bi-directional traffic flow through a layer-3 router. We purposely emphasized that this was for a production network and asked them to harden the configuration, but did not provide specific requirements. A mid-level engineer typically configures the VLANs in 10-20 minutes and says they are finished. But a senior engineer would take another 15-20 minutes to disable and assign unused ports to an unused VLAN, avoid using VLAN 1, configure user-facing ports as non-trunking, optimize spanning tree, configure VTP, configure switch security (such as BPDU Guard, Root Guard, DHCP Snooping, port security, etc.), harden access to the device, and many other configuration best practices. We basically designed a test that gave us insight into the depth and breadth of the network engineer’s skill. The more the candidate paid attention to these details, the more eager we were to hire them.

Not Just for Propeller Heads

These “show me” exercises aren’t limited to technical job roles. If you are hiring a product marketing or product management person, ask them to build a part of a go-to-market plan for a product. You could ask the candidate to put together one of the following components of a product go-to-market plan:

  1. Build out a launch plan for a new product
    1. Distribution and channel
    2. Marketing and communications
    3. Competitive positioning
    4. Sales tools
    5. Training and mentoring
    6. Customer success plan
    7. Target customers / segmentation
    8. Geographic expansion
  2. Build a model that segments a market for some common product of your choice (e.g., bicycles, refrigerators, cars, grocery bags, etc.)
    1. Target customers
    2. Product categorization / sub-categorization
    3. Value proposition
    4. Use cases
    5. Competitors

If you are hiring an accountant or a bookkeeper, create a fictitious business in QuickBooks (or your preferred accounting system) with a few customers and some high-cost inventory items. Then ask the candidate to create a sales order with multiple inventory items, convert items that shipped to an invoice, create an AR aging report, and receive payment from the customer. Take note of how much audit data (like product serial numbers, shipment tracking numbers, payment reference numbers, etc.) they capture in the transactions they record. Did the candidate know to ask about class tracking (a somewhat more advanced feature)? There are plenty of scenarios you can create to determine a candidate’s depth and breadth of knowledge. If you don’t have a strong accounting or finance lead to help you design the test, then at least use an off-the-shelf test from a web site like

How, Not What

Many people have had opportunities to serve in certain roles. Whether they have experience serving in the role is just one criteria. A smooth talking candidate will paint a rosy picture of their past roles with little verifiable information. Don’t just ask what their responsibilities were, but dig into how they did it. What was their approach? What process did they use? How did they govern and control the process? Did they create the process or did they just follow a process someone else created? Did they profit off of someone else’s groundwork? In a startup environment, the groundwork is rarely laid so the candidate will have to lay it themselves. Were they successful in growing sales because the market was growing and they happened to catch a rising wave? Or were they successful in growing sales in a down market? Dig into details. Don’t be afraid to spend 20+ minutes getting into the weeds with the candidate on how they did their job. I’ve met many, many candidates with Superman resumes, but Clark Kent abilities. It takes time and determination to separate the chaff from the wheat.

Stud or Dud?

Getting the right players on your fantasy football team requires knowledge and hard work. Every team needs a few star players that you pick in the first, second or third round of your draft. In fantasy sports, identifying the best players is somewhat easier because you have access to the player’s performance and stats from previous years. In addition, ESPN and other sports outlets provide a ton of advice on who to pick and when to pick them. However, in the world of startups, we don’t have access to stats or sports analysts who provide specific advice on individual players. Hopefully the suggestions above help you hire a few game-changing players for your team. In a future article, I’ll provide some suggestions for finding unproven talent to fill out the rest of your team.