IT project management software is judged in the second month, not the demo. By then the team knows whether the tool sits beside the work or in the way of it. Stack Overflow's 2025 survey found 54% of respondents using six or more tools to do their job, and Atlassian's 2025 developer-experience research found half of developers losing ten or more hours a week to organisational friction, with context switching between tools near the top of the list. A new tracker either removes some of that switching or adds to it. These eight requirements are how to tell which, before you sign.
1. 1. Tasks That Know About the Code
If a pull request or commit mentions a task, it should show up on that task without anyone pasting a link. In Kavanah, the GitHub App syncs repositories, pull requests and commits, and a title or message that says fixes #123, task 123 or TASK-123 links the record to that task, with its branch, state (draft, in review, merged or closed) and line counts. Ask any vendor exactly which phrases it recognises; a link that only works when someone remembers a special syntax will not survive a busy sprint.
2. 2. One Source of Truth for Bugs
Many teams keep bugs in GitHub Issues and plans in a tracker, and lose track of which copy is current. Require a two-way sync that is explicit about which fields it carries and how it avoids echoing its own changes. Kavanah's Issues sync is opt-in per repository, carries title, body and open or closed state, and nothing else, so the meaning of each synced field is the same on both sides.
3. 3. Estimates the Tool Can Check
A tool that stores estimates but never compares them with actuals cannot tell you whether your plans are honest. Require estimate-versus-actual reporting per person, and a planner that uses it. Kavanah measures the last 90 days of completed work and plans sprints at the median and at the 90th percentile without rewriting the stored estimates.
4. 4. AI Agents With a Scope, an Approval Step and an Undo
Every vendor now ships AI. The question is what it may touch. Require that an agent sees only the projects it is given, that you can make chosen categories of action wait for a person, that every action is recorded, and that a person can reverse one. In Kavanah those are project access, action policies, the action ledger and undo, and anything that runs on its own or spends AI credits starts switched off.
5. 5. An API, a CLI and MCP
IT teams automate, and increasingly they automate through AI assistants. Require a documented REST API, a command line and a Model Context Protocol server. Kavanah publishes an OpenAPI specification, ships the kvn command line and runs an MCP server that Claude can use as a connector.
6. 6. Identity Controls, and Which Plan Has Them
Single sign-on and directory sync are table stakes for an IT buyer, but they are often reserved for a top tier, so ask which plan carries them. In Kavanah, SAML 2.0 and OIDC single sign-on and SCIM are on the Enterprise plan; TOTP and passkey multi-factor sign-in and per-project and per-task access control are available to every workspace.
7. 7. A Straight Answer on SOC 2
SOC 2 reports cover security, availability, processing integrity, confidentiality and privacy, and your customers' security questionnaires will ask about every tool that holds their data. Ask whether the vendor has a report, which type, and for what period. Kavanah's SOC 2 Type II observation period is underway and there is no report yet; we would rather say so than imply otherwise.
8. 8. A Way In That Is Not a Migration
Moving a team's whole backlog is the riskiest week of any tool change. Prefer a tool that can work alongside the current one first. Kavanah connects to Jira, Asana, ClickUp, monday and Notion, and imports from Trello, monday and CSV when you are ready to move.
Run the eight questions against every shortlist, including us. The longer version, with a dated comparison against Jira, Linear, Asana and monday dev, is on our project management software for tech companies page.
