The worst delays start with innocent five-minute steps: copying data between tools, chasing a missing field, or reformatting a spreadsheet column. Each tiny pause multiplies across days, people, and priorities. Name them, measure them, and stack them into an automated routine that quietly returns whole mornings.
Watch for patterns like weekend catch-up marathons, skipped checklists, and Slack threads turning into ad-hoc ticket systems. These signals reveal processes that cannot scale beyond two heroic contributors. Surface them in a team review, agree on a single owner, and draft a lightweight action path with clear checkpoints.
Draw the actual path work takes, including detours for approvals, clarifications, and tool switching. Mark wait states with time estimates and highlight where decisions pile up. This simple map often shows a single recurring stall that one webhook, form, or daily job can remove entirely within a week.

Ignore marketing adjectives and evaluate the surface area: webhooks, REST endpoints, SDK maturity, and rate limits. Good documentation beats shiny dashboards in the long run. If your tiny team can automate integration tests for critical calls, you own your destiny instead of waiting on support tickets and sales promises.

Pick pricing models that are predictable and proportional to usage, not headcount. Show how a monthly fee replaces hours of repetitive work and reduces error-prone handoffs. When finance understands the savings narrative and risk reduction, approvals speed up, renewals stay painless, and your automation runway remains well protected.

Prefer systems that reveal failures clearly, support dry runs, and let you change configurations without arcane rituals. Your teammate should fix a broken step with a coffee in hand, not a weekend lost in forums. Maintenance simplicity compounds into confidence, faster experiments, and fewer abandoned, brittle integrations.
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