I think of a "retool" as having a similar definition to "rebuild" except you're trying to renovate rather than rebuild. I do think it requires a team actively making moves to change the makeup of the team rather than making moves that are more or less part of the normal course of business. I think it often does require the acknowledgement that the team might not be taking a step forward the coming season. And part of that comes from the belief that continuity is important. Can you think of a team that made massive changes to the roster over the summer and win a Cup the next year? Like we wouldn't commonly describe a Cup winner losing a lot of players to free agency as retooling. They're looking to win another Cup. Similarly, we wouldn't commonly describe a non-playoff team who made a lot of moves towards playoff contention as retooling. Certainly if say we decided to trade our first round picks for the next 5 years for immediate help would say that management made the decision to retool?
Simply adding players to fill holes in the lineup (e.g. a 2C) isn't a retool.
Making a lot of trades doesn't mean the team was retooling. Like trading a 1st for Perron. Trading mostly futures for Kessel. These aren't typically seen as "retool" moves. Trading Perron (who wasn't a fit and a pending UFA) for Hagelin (who was under contract and filled a need) also isn't a typical "retool" move.
That's just my opinion. I see Neal as the biggest retool move as they brought in a different type of player.
