Law Office of Ole Olson, PLLC · Helena, Montana

Trial-Tested. Government-Savvy. Technology-Fluent.

A rich practice before Montana's courts and administrative agencies, deep working knowledge of state government, and extensive experience advising corporations and law firms on AI and eDiscovery.

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Ole Olson, Attorney at Law

Three Areas of Focus

A practice built where Montana litigation, government, and legal technology meet.

Litigation & Appeals

Trial and appellate representation in civil and administrative disputes. A courtroom practice built over nearly two decades — jury trials, contested motions, and appellate advocacy before courts throughout Montana.

Government & Regulatory

Prosecution and counsel for the State, municipalities, and counties — and guidance for citizens and businesses navigating state government. Experience earned serving the City of Helena, dozens of county attorneys, a justice of the Montana Supreme Court, and two of Montana's constitutional offices — three Attorneys General and the Commissioner of Securities & Insurance.

Legal Engineering & eDiscovery

Advising firms and clients on AI-assisted workflows, eDiscovery strategy, and the defensibility of technology in legal practice — bridging what the tools can do and what the rules require.

Background & Credentials
Montana Supreme Court
Law clerk to Justice Brian Morris
State & Federal Prosecutor
Special Assistant U.S. Attorney; trained and advised Montana's prosecutors on their toughest cases
Governor's Award for Excellence
As Chief Legal Counsel, Montana Securities & Insurance (2023)
Legal Engineering
Advised corporations and law firms on AI workflows that are defensible under the rules of practice
Ole Olson

About Ole Olson

Ole is at his best in three places: in a courtroom, on both sides of state government, and at the seam where law meets technology. He tries cases and argues appeals. He advises agencies — and helps clients navigate them — with the perspective of someone who has led inside one. And he brings hands-on experience with the latest legal technology.

An engineer before he was a lawyer, Ole is fluent in both languages — as comfortable cross-examining an expert as reading the data behind the expert's opinion. He prepares a case the way engineers build: rigorously, with every assumption tested before it has to bear weight in front of a jury.

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Ready to Discuss Your Matter?

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Reviews from Google

What Clients Say

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  • I can’t say enough good things about Ole Olson. I had been representing myself pro se in a debt-collection case and was completely overwhelmed by how complicated and stressful it had become. Ole stepped in, took the time to understand the details, explained everything clearly, and handled the case with incredible thoroughness and care. He was responsive, straightforward, and clearly put a tremendous amount of work into protecting me and getting the case resolved the right way. The claims against me were ultimately dismissed with prejudice, and I could not be happier with the outcome. Ole did a kick-ass job, and I would recommend him without hesitation!

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Client reviews reflect individual experiences. Past results do not guarantee a similar outcome.