Tech Challenge Tips: A Proposal Manager’s Guide

As Proposal Managers, we know all the intricacies of exercising total command and control of the proposal development process; but mention the words “Tech Challenge” and suddenly we are unfamiliar and grasping for next steps.  

Broadly defined, a Tech Challenge (TC) is any hands-on coding exercise that requires submission of working code or access to a working application as part of the acquisition process. This may be one of various forms with inconsistent use of terminology: Coding Challenge, Technical Demonstration, or Scenario-based Coding Submission. All forms create a mostly unfamiliar set of complexities for both the proposal and solution teams. 

At best, we may consider ourselves tech-adjacent through managing proposals in alignment with corporate capabilities, such as DevSecOps; however, there are many complexities to organizing and executing tech challenges that we may never fully appreciate. In the end, it is still the Proposal Manager’s responsibility for ensuring compliance and on-time delivery of tech challenges and their outputs.  

So, how can we merge proposal management techniques without inadvertently restraining the tech challenge team to meet its full creative potential? The answer is to use a tailored, systematic approach that allows for some flexibility. The following best practices will help Proposal Managers navigate a commonly unknown territory with more ease. Those best practices include the following: 

Establish ground rules with your TC Lead. A TC Lead is similar to a book boss role on a standard proposal response. They are your insight into the make-up of the TC team (how each team member’s technical strengths complement the designated TC roles) and how well prepared they are. It is therefore essential that the TC Lead be a single point-of-contact so that communication may be streamlined between the Proposal Manager and the TC team. 

  • Establish a Tech Challenge Lead and hold a Kickoff. It is encouraged for the Chief Technology Officer (CTO), or a similar role, to identify the TC Lead. 
    • Pre-Kickoff. The TC Lead determines the TC team roster and schedule the TC Kickoff several weeks before the anticipated TC drop date. Expectations for the Kickoff are clearly communicated to the TC team. 
    • Kickoff. The TC Lead runs the Kickoff and includes at a minimum the following agenda items: 
      • TC’s role in Government evaluations and TC structure (take-home coding challenge, live coding challenges, etc.) 
      • Definition of a successful TC and what those wining factors are (evaluation criteria) 
      • Expectations for participation, working hours, and team communication during prep sessions and actual coding exercise(s) 
      • Guidelines on tool implementation and processes (identify tools early on) 
      • Development guidelines (definition of done) 
      • Individually assigned technical roles and responsibilities for each member 
      • Prep Sessions. The TC Lead monitors the prep sessions to ensure the TC team exercises best practices in addressing winning factors. 
  • Review processes and come to a consensus. Avoid headaches and frustration by agreeing upon ground rules that clarify the overlap of TC preparation and Request For Proposal (RFP) compliance.The first step in coming to a consensus is understanding how that overlap creates tension. There is a fundamental difference in how the TC team and the Proposal Manager views TCs: the TC team thinks first of working code that delivers a Minimum Viable Product according to the definition of done; while in contrast, the Proposal Manager thinks first of compliance.

    Bridging that gap is achieved through collaboration between the TC Lead and Proposal Manager to ensure the evaluation criteria is weaved into prep sessions, schedules are agreed upon, milestones for compliance checks are reasonable, format for reviews are streamlined, and lines of communication are clear.   

Apply effective role management from the very beginning. The underlying principle that will prove most beneficial throughout this process is to never assume roles and expectations are clear. This process is a blend of proposal and technical perspectives and requires additional clarification. 

  • Create a single team mentality through empathy. Each team (the proposal team and the TC team) understands their own roles and assignments, but most often that exists in isolation of each other. The Proposal Manager coordinates with the TC Lead to make the TC team aware of the proposal team’s purpose, which is to highlight the great work of the TC team and not to be the overly critical observer that adds stress to an already demanding TC.

    For instance, the TC team should understand that the proposal team needs time to coordinate the submission to ensure their hard work gets in front of Government evaluators. This means that the TC team should have a target code freeze to allow enough time for preparing the final package. Likewise, the proposal team needs to understand that a TC is not business as usual. Creating working code is very different from creating a compelling proposal response. Becoming comfortable with uncertainty will yield more value than trying to apply concrete deadlines. 
  • Establish ownership versus being a contributor for required documentation. TCs may require documentation in addition to a solution to a problem statement. It is important to specify exactly who is responsible for drafting the documentation (owner), who that person contacts for information to substantiate the documentation (identify one contributor per TC team role/function), and who participates in reviewing drafted documentation for technical accuracy. This will prevent the TC team from splitting their focus from the problem statement and worrying unnecessarily about what their role is regarding documentation.  

Make compliance iterative. A more flexible approach to compliance is necessary with so many simultaneously moving parts being completed in a non-linear fashion.  

  • Establish dependencies first. While code is being developed, you will not have most of the solution available to do a full compliance check. Keeping this in mind, discuss with your TC Lead the initial requirements that will be developed first so that you can build a logical schedule that follows the development lifecycle. 
  • Create a schedule with repeated milestones. Once the dependencies have been identified, create a schedule with repeated compliance checks that build on top of each other. Make note of exactly what will be reviewed during each check. 
  • Use continuous documentation. Everything is fluid, so documentation must follow suit. Certain types of documentation cannot be drafted until the very end, so you must adopt the idea of updating drafts incrementally. For documentation that can be completed earlier, conduct compliance checks for technical accuracy and sections L and M as they are written. 

Become familiar with the process. Lastly, there are methods to familiarize yourself with the TC process so that you have a better understanding of how to prepare. 

  • Discuss Proposal Manager’s role during ramp-up. Have frequent and broad-ranging (in terms of participants) discussions on what the ramp-up for preparing for TC prep sessions involves and where your role may help provide support. Use these as an opportunity to reinforce the responsibilities that you own, as well. 
  • Attend prep sessions. Sitting in on prep sessions is the best way to see how the TC team works and communicates. Seeing this end-to-end process allows you to assess strengths that can be showcased on demonstration day, improving the team’s ability to provide a compelling presentation. Being present also shows your commitment to the team’s overall success and creates trust. 

Author Info

Lisa Holley, CP APMP, is a Proposal Manager at Pyramid Systems, Inc. She has a bachelor’s degree in Political Science from American University and can be reached on LinkedIn. 

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