In my activities as an angel investor, and my work with new ventures seeking investment, I find the "due diligence" stage to be fraught with the most risk. Usually this stage only really starts after an investor has expressed serious interest, or already informally agreed to invest.
Most founders consider the story already told and the deal pending, so they aren't sure what more then can do.
Others schedule long and exhaustive practice and coaching sessions for everyone on the team, including showcase customers, to make sure that everyone tells the most positive and consistent story.
Trying to stack the deck probably won't work, but some effort makes sense, since I have personally seen more than one deal fall apart due to key team members being totally out of sync.
My best advice is to put some structure and discipline into your due diligence preparation, including the following steps:
1. Schedule a team meeting to bring everyone up to date.
This meeting should include the CEO giving the investor pitch to the whole organization, and distributing the current business plan document to everyone. Since due diligence will include one or more visits from investors, everyone needs to be on the same page, with no surprises.
2. Identify and resolve any pending personnel situations.
You need to brief the investor early if there are organizational or people changes that are in process, or conflicts that may become apparent during the due diligence visits. Make sure everyone accurately posts their role with your startup on social media profiles, resumes, and references.
3. Set up an interview room, stocked with current documents.
The right preparation--including the latest business plan, organizational charts, process documentation, and an assigned executive other than yourself who can explain all of them--will go a long way in speeding up the process and creating a professional impression. Be prepared to follow-up as required.
4. Ask each of your leads to prepare for an interview.
Investors or their consultants will expect to talk to several key personnel, looking for an update on how the business really works, depth of skills, culture, traction, and action plans.
It's fair for you to ask for a few slides from each in advance, and make sure the overall story is complete and consistent.
5. Update reference customers, partners, and vendors.
Use this opportunity to validate their satisfaction and support for your company and your solution. If you find open issues that can't be immediately resolved, be sure to proactively communicate these to investors, with an action plan, rather than try to hide or gloss over them.
The key theme for a successful due diligence is full disclosure and no surprises before or after the commitment. If more potential marriages were subjected to the same rigor, the divorce rate would likely not be in the current 50 percent range.
In business as in other relationships, people on the team have to be above reproach, committed, and working on the same goals and values.
Startup equity investments imply a long-term business relationship, lasting five years or longer. During that period, it is very difficult for either party to get out of the deal, since there is no public market for the stock, and business divorces normally mean bankruptcy.
It's worth your time to do a little extra work here, and make the honeymoon phase a win-win one for both sides.
You need to remember that investor meetings up to this point have been primarily off-site, with staged demos, and managed personally by the CEO or one or two executives. Due diligence reverses this process to include on-site visits and informal discussions with any or all members of the team, vendors, and good customers as well as bad.
Based on the size of the investment, and the runway available, the due diligence process can take several weeks, or even a couple of months to complete. Of course, it's always appropriate to concurrently and openly reverse the process on your potential investor.
A relationship as important as this one should never be a one-way street. Make it work for your new venture.