Best practices for prompting Doow AI

How to write effective prompts, troubleshoot inaccurate answers, and get the most from Doow AI.

Doow AI gives you the best answers when you ask clear, specific questions. This article covers how to write prompts that get you precise results, and what to do when an answer does not look right.

Writing effective prompts

Be specific about what you want

The more precise your question, the better the answer.

Weak prompt	Strong prompt
"Show me spend"	"How much did we spend on engineering tools in Q1?"
"What about Slack?"	"How many active Slack users did we have last month?"
"Any savings?"	"Which applications have unused licences worth over $500 per month?"
"Renewals?"	"What subscriptions are renewing in the next 60 days, sorted by amount?"

Include the dimension you care about

Tell Doow AI what to group or filter by: application, department, category, time period, or spend type. If you do not specify a time period, Doow AI defaults to the current month.

"Break down marketing spend by application this quarter."
"Show me utilisation by department for all collaboration tools."
"Compare spend on annual vs monthly subscriptions this year."

Name the metric

If you want a specific number, say which one: spend, users, utilisation percentage, renewal count, savings amount.

"What is the average licence utilisation across all apps?"
"How many apps have zero active users in the last 60 days?"
"What is our total annual committed spend?"

Ask one question at a time

Doow AI works best with a single question per prompt. If you have multiple questions, ask them in sequence as follow-ups. The AI remembers the context from earlier in the thread.

Less effective: "Show me Slack usage and also what our top 5 apps are and when our next renewal is."

Better: Start with "How many people used Slack in the last 30 days?" then follow up with "What are our top 5 apps by spend?" then "When is our next renewal?"

Use follow-ups to drill down

After an initial answer, use follow-ups to refine:

"Just show me the marketing department."
"Break that down by month instead."
"Exclude any app under $100."
"How does that compare to the same period last year?"

Doow AI answers are only as current as your last integration sync. If an integration has not synced recently, the AI may be working with stale numbers. Check the last synced timestamp at the top of the AI response — it shows which integration provided the data and when.

To force a re-sync, go to Settings → Integrations, find the relevant integration, and click Sync now. Wait for the sync to complete, then ask your question again.

Unmatched expenses

If expenses from your bank or accounting feed could not be matched to an application, they are excluded from the AI's analysis. The AI flags this: "Note: $X in unmatched expenses were excluded." To fix, go to the Expenses page and match the unmatched transactions. The AI will include them in future answers.

Scope and filters

The AI respects any filters currently applied in your session. If you filtered the dashboard to a specific department and then asked the AI a question, it scopes the answer to that department. If the answer seems too narrow, check whether a filter is active — a small tag appears next to the AI input when filters are active. Click the tag to clear it.

Asking the AI to double-check

If a specific number does not match what you see elsewhere in Doow, ask: "How did you calculate that?" The AI will walk through its reasoning, including which data sources it used and which filters were applied. This usually surfaces the discrepancy.

If the number still looks wrong, open the relevant page (Applications, Expenses, or Subscriptions) and compare the figures directly. If there is a genuine discrepancy, report it to support via the in-app chat.

What Doow AI cannot do

Doow AI answers questions about your data, but it has limits:

It cannot modify data — you cannot ask it to "delete the Datadog subscription" or "change the category of this expense." Use the relevant page for data changes.
It cannot send emails or notifications — it will not "email the renewal list to my manager."
It cannot access the web — it will not "look up current Datadog pricing."
It cannot create reports — for scheduled, formatted exports, use the Reports page. The AI can help you build the right filters, then you can open Reports and save them.

Keeping threads organised

Your AI conversation history can grow quickly. A few habits keep it manageable:

Start a new thread for each topic (e.g. one for renewal planning, one for utilisation review).
Give threads descriptive names — click the title to rename. "Q3 renewal prep" is better than "Question about renewals."
Delete threads you no longer need from the thread menu. This keeps your sidebar clean.