How to Kick Off a Project

First impressions really do matter. As an independent contractor, you’ve likely already met most of your key stakeholders during your sales cycle. But you aren’t on the hook for anything until that contract is signed and you’re beginning to kick off the project. The kickoff meeting is your chance to make a great impression and show that they made the right decision entrusting this project to you. Based on seeing hundreds of project kickoff meetings, here are some best practices for you to employ.

Invite the Right Audience

Based on your expertly executed sales process, you should have a pretty good idea of who all needs to be included in your kickoff meeting. If you’re unsure, find out from your main point of contact so that you can be sure you don’t run into an awkward situation of “Oh, we should have invited Kathleen.” Not a great way to signal a shared vision for the project.

Here are some individuals you’ll want to consider inviting:

• Your main point of contact: This one seems pretty obvious. Prep them ahead of time, and get some pointers from them. Understand the political environment. Depending on their role & influence in the company, you may need to lean on this person to add credibility to the project.
• The executive stakeholder(s): The money for your project came out of someone’s budget. Make sure that person attends the meeting and feels like their money is being well spent. Invite any other executives who might be listed in the “informed” category on a RACI chart.
• The “doers”: This one depends on the size of the team you’ll be working with. If there are only a couple of people that will be involved in the project, make sure they’re on this call. Ensure they feel like a critical part of success. If there are lots of people working on this project with you, consider scheduling a separate meeting. The initial kickoff will be a high-level objective-setting session and the follow-up will be a tactical kickoff.
• Executive assistants: Again, this depends on how big your project is. Include an executive/admin assistant if you need consistent time with busy executives or if your client sources all scheduling through one individual.
• System owners: In the case of a smaller project, you may be able to cut your ramp up time by making sure the relevant system owners are on the call to get you the access you need, set up SSO, create a shared Slack channel, or handle any other technical tasks that may come up.

Research the Client and People

If you’ve made it this far in your process, you sure as heck better know a lot about your client and your key stakeholders. But research doesn’t stop once you’ve made the sale. Use the kickoff as an impetus to learn more about the people involved.

You should feel confident on all of these topics going into your kickoff meeting:

• The basics of the company, including headcount, revenue, and funding status
• The products they offer and how they differ from their competitors
• The state of the security/compliance function
• Any past/failed security/compliance initiatives
• The top-level business driver for this project
• The size of the business pain you are solving
• The people with a vested interest in your project
• The organization’s structure (both the on-paper structure and the implicit power structure)
• The roles, history, and attitudes of everyone on the kickoff call

Send an Agenda

An agenda is fundamental to a well-run meeting. Even if nobody reads it ahead of time, you’ll accomplish two majors things by preparing an agenda:

1. You will force yourself to sit and reflect on the client, the project, and the associated goals.
2. You’ll give your client confidence that you take this project seriously and want all parties to be successful.

You should have an agenda template that you can quickly plug in key client info into. I’ve seen success with agendas in emails, as Word docs, and as slide decks. It ultimately comes down to your style. Just be sure your agenda includes:

• Time for introductions.
• A reminder of the corporate objective.
• An overview of the timeline (including any dates where people are unavailable).
• Any technology needs.
• Immediate next steps.

Help Them See the End Goal

No one does compliance for fun, and very few people do penetration testing for fun. There’s always a corporate goal that your project ties back to. Your client is either trying to drive revenue growth, reduce costs, or measurably decrease their risk. Paint a clear picture of how your project ties into whatever that corporate goal is. In turn, you’ll gain the respect of your executive stakeholders and you’ll help align the rest of the project team with their business’s objectives.

Start with a Win

Everyone should leave the kickoff meeting feeling like they got something from it. For some, it may just be confidence that they chose the right person for the job. Ideally though, you either give them some new insight or you make visible progress on the project.

For example, you may discover some things in your research that are worth sharing. Perhaps some information around a competitor’s compliance initiatives, or some new mandate coming soon that could affect them. It could also be an insight on how the project team can best approach the project based on their skill sets.

Your other option, which frankly is more of a given, is to make progress on the project. In the case of a large project, this may simply be scheduling a weekly status call or a logistics call with the right audience to plan out the rest of the project in detail. For a smaller project, though, you have an opportunity to build on your momentum very quickly. Set aside some time to schedule very specific calls that will move the project forward. In some cases, you may be able to roll directly into your very first information gathering session. Use this chance to get creative and give the client something to get excited about.

Have the Next Meeting Booked

This principle should apply throughout your entire time with the client - from the initial sales call all the way to closeout, and potentially beyond if the client is considering renewing with you. Coming out of the kickoff meeting, everyone should know their next steps. You’ll likely need to move into a planning meeting to get the rest of your meetings scheduled. For a small team, you may be able to save a step and book your first meeting directly.

No matter the nature of the project, your goal at this point is to keep the momentum going. Without someone driving the project forward, the nature of corporate projects is to sputter and die. Don’t let that happen. Stay connected with your client’s business objectives and work with your key stakeholders to drive the project to a successful completion.