Planning is hard work. Make no bones about it—creating a yearlong outreach plan for your annual giving program can be the most difficult task you perform all year.

Too often, though, I see shops using the results they need (number of donors and number of dollars) as a guiding light. Instead of tying the year together with a strategy or theme, we send one-off pieces as needed. We treat each solicitation like a checkpoint that informs the next step.

You’re down on LYBUNTs? Send another letter! You’re up with SYBUNTs? Focus on another area.

And on and on.

This isn’t to say there’s no value in these checkpoints, but my experience has taught me that creating a comprehensive, yearlong plan is the best way to stay on track and get results.

Below I’ve mapped out the questions you should ask yourself as you plan for the fund year.

How much outreach will you do?

Yes, I’m suggesting that—at the start of the year—you should plan the number of solicitations and/or stewardship pieces you will send.

You’ll always have to leave some wiggle room, but for most constituent bases, there’s a sweet spot of outreach that you’ll want to hit. How often do you want them to get direct mail? Email? Phone calls?

Planning this number in advance will help you make sure your constituency hears from your institution enough and in the right way. And this leads nicely to the next question…

When will you send each solicitation?

This may seem like an easy question, but it was often the most difficult for my team members to answer.

To start, look at your data for the following pieces of information:

• How long of a run does each mailing have? How about each email?
• How many gifts come in from letters? From emails?
• How much volume do you get from checks? Stock gifts? Online donations?
• When do these solicitation methods typically peak?

Digging into these data points will help you determine when it’s best to send what. For example, if you see a large volume of gifts from emails during a specific month, target that month for one of your e-outreaches. If your mail pieces tend to work for three weeks, think about sending follow ups at the four-week mark to increase the run.

Arranging your solicitation calendar ahead of time should help you with the next question.

Who will you send to?

Resources are hard to come by. You never seem to have enough money, time, or talent for all of the things you hope to do—which is why it’s so important to understand where you’ll see the most ROI from your outreach.

As much as we would all love 100 percent participation, planning your year around that goal may not be the best use of resources. Instead, find the groups who are most likely to give and target them at the proper times.

Who are the constituents that can make a difference? Divide them into manageable segments that make sense for your institution, and then move on to the next question.

Sample Segment for EverTrue Users

What will they get and who will it come from?

So, that makes two questions… but they fit together well. Does a constituent group give the majority of gifts online? Do they give most through direct mail? Do they give because the president asks? A classmate? A faculty member?

Planning what each of your constituent groups will receive over the course of the year will help ensure that each group has a touch from all of the possible voices, messages, and mediums they might respond to. From my experience, I’ve found that the more variety in each of these areas, the better chance you have of securing gifts. This is your chance to be creative!

Keep in mind: not everyone has to make a gift from every piece of outreach. Don’t try to eat the whole elephant at once. Variety will help ensure you have the best odds to secure the most donors and cash by the end of the year.

This sets you up to answer the final question.

What special projects or areas will you need to solicit for?

As advancement offices, we only have so many opportunities to reach out to our constituencies. Special projects and one-off giving opportunities can be great, but they take away touches from our broader annual priorities.

With that in mind, make sure you know (as much as you possibly can) what specific projects you’ll be soliciting for during the year. This lets you build these solicitations into your master plan instead of building your plan around them.

Planning is a challenging process. But if done right, it makes everything else much easier.

Remember, we are in a yearlong business. Each layer of outreach should add onto the last. Being deliberate and intentional with each will make your year end much less stressful and much more fruitful.

Happy planning!

Josh Foladare is the senior director of alumni relations and annual giving at St. John Fisher College and formerly the director of annual giving at Hobart and William Smith Colleges. When he is not helping raise money to make the colleges great, you can find him brainstorming new ways to explain what he does at work to his friends and playing with his two rescue dogs. Connect with him on LinkedIn.