Ops Insights #065 - Learn and Gain Confidence 3x Faster

May 14, 2025 | Read Time: 6 minutes | Written by Jenny Kleintop

I believe confidence comes with practice, and it’s the type of practice you get that allows you to get confident faster. For example, early on in my career, I took the long route. I dove into online documentation, courses, and tutorials all on my own for days before I attempted to do something. I read, studied, and then read and studied more before attempting to do database set-up, configuration, imports, or list pulls. For some reason, I thought I had to know every little detail before diving in.

You know what? That took a ton of time that I did not have. So when I went to work for my second nonprofit and my boss offered to hire a consultant to help me do a conversion, I said yes. I was tasked with converting two databases into one new database that we were acquiring which I had not used before. And we had 6 months to do it. I followed my old habits of diving into documentation and courses online and remember taking 60 classes in 30 days. I even jumped into the vendor’s community and read as much as I could. I was determined.

Then, in month two, I started working with the consultant to learn how to set up the new database in the best practice way. Many light bulbs went off as I leaned in and learned. In those 3 months that followed I was able to learn 3 times faster than I would have on my own and felt confident I was setting things up properly as I was working off his years of experience studying and applying best practices.

Here’s what I discovered:

1. Go solo and you’ll learn and gain confidence.

2. Go via community and you’ll learn and gain confidence even faster.

3. Go 1:1 with an expert and you’ll learn and gain confidence 3x faster.

I believe you don’t have to pick only one of the three options. Use all three. I still do to this day. Depending on what you are tasked with and where you have to get to and how quickly, pick the right option for you.

Just make sure not to be afraid to ask for what you need.

All these years later, I’m in that seat helping others gain confidence and go 3 times faster. Here’s what I tell them… don’t be afraid to get it perfect or mess up, just go for it. Often, it’s me showing up, leaning in alongside them and giving them that confidence to go for it. Slowly, I quiet down as we work more and more together and I see them gain that confidence quicker than they would have on their own. And I love it! I absolutely love seeing someone go from “I have no idea” to “I got this.”

The majority of the things you do are fixable. Yes, you will mess up sometimes, but you just need to learn how to fix it. For example, I meant to delete a field from an export and I deleted the whole export because I was moving too fast. The world did not fall apart. I pulled up my excel sheet that I had exported during the last run and I quickly re-build the export. Things are generally fixable.

Here are 4 things I’ve helped with lately to give confidence to go for it. Learn, gain confidence, and then go for it. Don’t let the fear of messing up stop you. If you don’t know how to fix it, then find someone who can help you.

1. Imports: Map the columns and go for it. Tip #1: Add unique import IDs to the section you are importing (ex. appeal import IDs, action import IDs) as even though they are not required, it helps if you need to fix or update after the import. Tip #2: If you have multiple imports to do, run them at the same time, and keep another database version open so you can do other work while they are importing.

2. Global updates: Love these as it’s easier than imports. When you have a quick update and don’t want to have to do a lot of mapping, global updates can be your friend. I’ve used them lately to update GL post dates, add gift attributes, and add constituent appeals.

3. Export/Import: Another way to update data is to export it, update the column, then import it back in. Constituent IDs were way too long and CSV files did not like them. So I exported them, sorted by date added, added a column for the new constituent ID counting 1 up to 149K. Then imported back in to update all the IDs. Tip: Add the old constituent ID as an alias with a unique type. This way if you have old lists floating out there, anyone can still look up by alias. Then about 6 months later you can delete the alias to clean up the database.

4. Campaigns: I’ve done it at 4 different places over the past year. Campaigns are a way to show overall progress toward fundraising goals and should align with strategic initiatives. I’ve re-aligned them, tagged goals on them, and then updated gifts for this fiscal year and last fiscal year for comparative analysis. Tip: Use this in comparative dashboards to visually show progress year over year.

Take Action

Figure out where you can go solo, where you can dive into community, and where you could use 1:1 help to go 3 times faster. Then ask for what you need and go for it.

1 ➡ Make a list of all your to-dos, tasks/requests, short-term, mid-term, and long-term projects. Everything, write-it out. Ideally you already have a data request tracking sheet or program. Even compile the activities from last year that are likely to need repeating. Then add items from your strategic plan, goals, wish list, and things you’ve heard or said yourself we need to _____.

2 ➡ Now organize that in two ways. First by priority (high, mid, low), and then by type or duration you have to do it (data request, short-term project, mid-term project, long-term project).

3 ➡ Then add a column for how best to tackle it, meaning by learning curve and confidence to do it on your own, through community, or better for 1:1 help. Remember, many times you can say you can figure it out (trust me, that was me) and you likely can but if you can get help and go 3x faster while also gaining 3x more confidence, then that opens up space for your other projects.

4 ➡ Finally, go talk to your boss. Show high-level, bullet type format. Meaning take your long and detailed list and structure it for a CDO to digest. Then have the details if that CDO asks for additional context.

Here’s an example:

• Short-term high-priority projects that I am confident I can get done by X date:

  • Update all constituent IDs (benefit: more usable when exporting data).

  • Project 2

  • Project 3

• Short-term high-priority projects that I am confident I can figure out, but could go 3x faster if we bring in help so we can make sure to get it done by X date:

  • Revamp our campaigns (benefit: better align to our strategic goals and improve reporting progress).

  • Project 2

  • Project 3

You’ve got this!

👋 See you next time,

Jenny

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